Gloucester Rentals
- From $475 per night (USD)
VRBO
Magnolia Ocean View Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Comfy cottage with stunning ocean views in the heart of Magnolia village. Convenient to beaches, stores and restaurant ...
From $475 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Luxury Home in the Heart of Rockport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! This home is located on a quiet ...
From $575 per night (USD)Expedia
- From $362 per night (USD)
VRBO
Ocean View - Great Location | Beautiful, Warm & Spacious.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Sun-filled vacation house with water view in the beautiful Magnolia town in Gloucester. MA (CAPE ANN). This charming, b ...
From $362 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Beautiful Spacious Colonial by Long Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful spacious Colonial in quiet neighborhood within walking distance to Long Beach. Brand new to the rental market ...
From $400 per night (USD)VRBO
- From $883 per night (USD)
VRBO
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
This is the Vacation Beach House you have been searching for. Perfectly located only steps to Long Beach Gloucester, thi ...
From $883 per night (USD)VRBO
- From $557 per night (USD)
VRBO
Waterfront Home with Spectacular Viewsof the Annisquam River
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Watch the beautiful sunsets over the Annisquam River from the deck or just enjoy the scenic views all day long of Pierce ...
From $557 per night (USD)VRBO
- From $618 per night (USD)
VRBO
Elegant Bayview Victorian Home - Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the color ...
From $618 per night (USD)VRBO
- From $265 per night (USD)
VRBO
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
My husband and I want to assure you that we take your family's health and safety very seriously. Our house is professio ...
From $265 per night (USD)VRBO
- From $905 per night (USD)
VRBO
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & seclude ...
From $905 per night (USD)VRBO
- From $1179 per night (USD)
VRBO
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private, newly renovated beach house on hilltop overlooking two mile white sand Wingaersheek Beach with access and 5 car ...
From $1179 per night (USD)VRBO
- From $427 per night (USD)
VRBO
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This recently renovated beach themed 3 level, 3 bedroom, 2.5 baths, fully stocked condo, has 2 unique outdoor spaces, an ...
From $427 per night (USD)VRBO
- From $639 per night (USD)
Expedia
PREMIUM PROPERTY - Private 2-Acre Retreat - MODERN 4 Bedrooms - See Video Tour
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
*NEW: We recently completed a full upgrade and modernization of the kitchen. In addition, we just completed a massive l ...
From $639 per night (USD)Expedia
- Click For Pricing
VRBO
Charming Gloucester Escape w\/ Private Garden!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
If you’re traveling to the East Coast, look no further than this 3-bedroom, 1-bathroom Gloucester home! This lovely vaca ...
Click For PricingVRBO
- From $269 per night (USD)
Expedia
Walk To Good Harbor, OCEAN VIEWS, Open All Year!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: You and your family cannot beat this amazing Gloucester location, walking distance to the best beach in all of ...
From $269 per night (USD)Expedia
- From $156 per night (USD)
VRBO
WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come to the Cape named after a Queen NOT an Ugly Fish!! 🤣FABULOUS, quiet, dead end location! Incredible views of the An ...
From $156 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Ocean Views in this Charming 2 bedroom Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Charming two bedroom cottage. The property has a wonderful open kitchen and dining room that gives way to an ocean facin ...
From $270 per night (USD)VRBO
- From $298 per night (USD)
VRBO
River's Edge: A charming 2BR riverfront home in Gloucester.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Exquisitely renovated by the owner-architect, every detail of this charming vacation home has been thoughtfully consider ...
From $298 per night (USD)VRBO
- From $714 per night (USD)
Expedia
Ocean front and 3 beaches across ,parks, short walk to historic downtown!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy ocean front by staying right on the Boulevard of Gloucester with an amazing location and ocean views from the fron ...
From $714 per night (USD)Expedia
- From $945 per night (USD)
VRBO
Bell View: Private tennis court and an in-law suite.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate u ...
From $945 per night (USD)VRBO
- From $325 per night (USD)
VRBO
4 Bedroom LUX House\/with Pool Next Door
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Nestled on private street in beautiful West Gloucester, this large vacation rental (you get the entire house-- not just ...
From $325 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Dock!! 40' Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Mooring is located on it's own peninsula surrounded by water in a unique section of Gloucester called Rocky Neck. R ...
From $850 per night (USD)VRBO
- From $469 per night (USD)
VRBO
BEACH! Good Harbor NEW CONSTRUCTION!!!!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy this new home with roof top deck overlooking Good Harbor Beach. We are a 5 minute walk to the beach! We ...
From $469 per night (USD)VRBO
- From $677 per night (USD)
VRBO
Featured on HGTV's Beach Hunters
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Golden Cottage by the Sea, is a true New England Cottage that has been lovingly restored and updated. This quaint 1830's ...
From $677 per night (USD)VRBO
- Click For Pricing
VRBO
Private, Light Filled & Convenient Wingaersheek Beach Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming, private, light filled home with newer addition in quiet neighborhood near Wingaersheek Beach. Large Master be ...
Click For PricingVRBO
- From $575 per night (USD)
VRBO
Evensong: Oceanview Retreat with Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unobstructed Water Views of The Annisquam in this newly-renovated "walls of glass" home boasting panoramic views of The ...
From $575 per night (USD)VRBO
- From $431 per night (USD)
VRBO
The Nest at Pigeon Cove: Modern farmhouse with all the comforts of home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Visiting Salem for Halloween? Take the train from Rockport and avoid the horror of Salem traffic! Nestled in the Pigeon ...
From $431 per night (USD)VRBO
- Click For Pricing
Expedia
Walk to Good Harbor Beach and Downtown Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy easy walking access to Good Harbor beach, downtown Gloucester, and everything Cape Ann and the North Shore has to ...
Click For PricingExpedia
- From $200 per night (USD)
Expedia
A tranquil ocean retreat steps from the water's edge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
On the Cove is a spacious three-room apartment is located directly on Lanes Cove in Lanesville (Gloucester) with spectac ...
From $200 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Sunset Views, Waterfront Property, Dock - Sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Stunning sunsets, a parade of boats going by, a charming marina, and a beach brimming with natural beauty — these are th ...
From $339 per night (USD)VRBO
- From $212 per night (USD)
Expedia
Holbrook House: Charming Rockport Village House, Walk To Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A cozy, lovingly restored 1950's house. Walking distance to all that Rockport village and Bear Skin Neck has to offer. ...
From $212 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
The Ledge House is a charming mid 19th century farmhouse situated below a large granite ledge in the village of Bay View ...
From $325 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Good Harbor Beach Apt.- 6\/10 mile walk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom apt.- sleeps up to 4 ( 2 adults, 2 children) Bedroom has a queen size bed replaced in 2017. The livin ...
From $179 per night (USD)VRBO
- From $297 per night (USD)
VRBO
Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our adorable, 3 bedroom home is in a prime location for your vacation, with plenty of windows for ocean breezes or if y ...
From $297 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summer at its best! A delightful spot near the beach, nice private fenced in backyard, walkable to Long Beach and Good H ...
From $425 per night (USD)Expedia
- From $322 per night (USD)
VRBO
Seaside Village of Lanesville - North Gloucester, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This quaint, cozy, quiet two bedroom fully furnished apartment in the Village of Lanesville has views of the Ipswich Bay ...
From $322 per night (USD)VRBO
- Click For Pricing
Expedia
Stanwood Point: Waterfront cottage with dock, large screened porch, and yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large 3 bedroom waterfront cottage on the Little river with a tidal dock. Large fireplaced living room, huge screened po ...
Click For PricingExpedia
- From $817 per night (USD)
VRBO
Elegant Italian Villa On The Scenic Coast of New England
- Bedrooms:
- 6
- Bathrooms:
- 10
- Sleeps:
- 18
Villa Fiori in scenic Manchester-by-the-sea is a short walk from local Black & White Beach and a 3 minute drive from the ...
From $817 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Lanesville Cove Retreat Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our serene, open floor plan home features everything you need for a short stay or a long term get away. Our goal was co ...
From $232 per night (USD)VRBO
- From $210 per night (USD)
VRBO
Private, Single Family Beach House, Right at Good Harbor Beach foot bridge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Real beach house on one of Boston areas most beautiful and clean beaches. This is a well-maintained, three bedroom, sing ...
From $210 per night (USD)VRBO
- From $108 per night (USD)
VRBO
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Om Suite Om is a comfortable, cozy and convenient studio efficiency space, with a separate key and entry, in the lower l ...
From $108 per night (USD)VRBO
- From $950 per night (USD)
VRBO
⭐️ Beautiful 4+ Bedroom Annisquam W\/ Private Beach Access 🏖
- Bedrooms:
- 0
- Bathrooms:
- 5
- Sleeps:
- 12
This a beautifully constructed, family-friendly 4 bedroom, 4 full bathroom home in the heart of Annisquam, one of the mo ...
From $950 per night (USD)VRBO
- From $514 per night (USD)
VRBO
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
This finely maintained summer cottage built in the 1820s overlooks Hodgkins Cove in Gloucester Massachusetts. Unique an ...
From $514 per night (USD)VRBO
- Click For Pricing
VRBO
Rockport direct Waterfront 3 bedroom, 3 bathroom home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious contemporary home offering direct waterfront location in quiet, residential Pigeon Cove neighborhood just north ...
Click For PricingVRBO
- From $331 per night (USD)
Expedia
Lovely 'Blue Heron Cottage' on Annisquam River!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located less than 5 miles from beautiful beaches, popular parks and local hot spots, the ‘Blue Heron Cottage’ is the per ...
From $331 per night (USD)Expedia
- From $916 per night (USD)
VRBO
Elegant Gloucester Beach Getaway with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for ...
From $916 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just a few steps to a white sandy beach called 'Long Beach' you will immediately be drawn to the gorgeous views of 'Twin ...
From $425 per night (USD)Expedia
- From $168 per night (USD)
VRBO
\"Rocky Neck Hideaway\" on Wonson Cove, Rocky Neck - Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<b>Enjoy the ambiance of a New England Seaside Getaway, without the crowds!</b> This charming, romantic one bedroom tow ...
From $168 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy your vacation sojourn in this newly-renovated home, a short walk to one of New England's most beautiful beaches. ...
From $315 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Bayview Guest Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
This property is a 650 sq. foot cozy cottage on Ipswich Bay with unbeatable views facing west, making for beautiful suns ...
From $395 per night (USD)VRBO
- From $768 per night (USD)
VRBO
Waterfront Wingaersheek Beach Unobstructed Panoramic Ocean and Lighthouse Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At the end of a road, perched on rocks, this remarkably sited year-round waterfront home accesses sparkling smooth white ...
From $768 per night (USD)VRBO
- From $813 per night (USD)
VRBO
Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
A spacious, beautiful contemporary home on a private oceanfront estate near Gloucester's coveted Annisquam district, wit ...
From $813 per night (USD)VRBO
- From $385 per night (USD)
VRBO
WaterViews Overlooking Gloucester Inner Harbor \/Sunroom\/ Deck \/Walk to Town\/ AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all ...
From $385 per night (USD)VRBO
- From $526 per night (USD)
VRBO
Summer Cottage on Ipswich Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This quiet summer cottage was built in the 1890's, it's original charm has been retained, while updates have made it a c ...
From $526 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Seaside Escape just steps to Good Harbor beach in Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Charming 2 bedroom home located on a quiet Cul de Sac that's just steps to beautiful Good Harbor Beach. Completely renov ...
From $381 per night (USD)Expedia
- From $319 per night (USD)
VRBO
♥ 2 Bedroom+Office|Minutes to Good Harbor+Rockport|Fast Wifi|Off-Street Parking♥
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
- Cozy + historic (pre-1900!) apartment with 2 bedrooms - High Speed wifi + private office for your "work-cation" - New ...
From $319 per night (USD)VRBO
- From $186 per night (USD)
VRBO
Ocean and Woods! Best of both seaside delights in Gloucester!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
If you are a nature lover, you'll love our location. 200 yards or so in either direction will lead you to treasured hab ...
From $186 per night (USD)VRBO
- From $277 per night (USD)
VRBO
WALK TO BEACH! Convenient location! Beautifully updated!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Look no further! Be one of the first to stay at this never before rented, stylish beach bungalow! It is the perfect vaca ...
From $277 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Harbortown Hideaway: Charming home in downtown Gloucester with water views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Gloucester's Harbortown neighborhood, the name Harbortown Hideaway perfectly suits this vacation rental. A ch ...
From $383 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Home, Private Dock, Ocean Access, 4+ Bedroom, 2 Bath, Porch, Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Unforgettable New England waterfront experience in this tri-level converted cottage situated directly on Little River, j ...
Click For PricingVRBO
- From $303 per night (USD)
VRBO
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Changes in Latitude is a perfectly located vacation rental home for your Gloucester beach getaway. The house is an updat ...
From $303 per night (USD)VRBO
- From $188 per night (USD)
VRBO
Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Are you ready to sit back, relax and enjoy all that Gloucester has to offer? Then this desirable East Gloucester apartm ...
From $188 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Historic charm meets contemporary comfort at Pigeon Hill.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Steeped in history, this traditional early victorian home has been newly remodeled and renovated blending original detai ...
From $234 per night (USD)VRBO
- From $272 per night (USD)
VRBO
Nature Lover's Paradise: cozy couples\/families, near town, nature walks, HiSpeed WiFi, 3 Smart TVs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
As you arrive at Serenity, you're welcomed by a beautifully maintained neighborhood. Then you enter a meticulously main ...
From $272 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Artist's Studio turned Guest House Sleeps up to 3
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
One room guest house with French doors leading to spacious deck, ocean views, less than 1/2 mile walk to Back Beach, vau ...
From $130 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Spacious Modern Beach House- Steps to Long Beach and Good Harbor
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Just steps to Long Beach, or a 10 minute walk to Good Harbor Beach, enjoy this clean, modern new single family home with ...
From $600 per night (USD)VRBO
- From $183 per night (USD)
VRBO
Come home to Rockport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Spend a weekend or a week enjoying the beauty and culture of Rockport. Enjoy panoramic views of Sandy Bay.and Straights ...
From $183 per night (USD)VRBO
- From $676 per night (USD)
VRBO
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectac ...
From $676 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Just 4/10 of a mile from Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestle ...
From $245 per night (USD)VRBO
- From $714 per night (USD)
VRBO
Good Harbor Beachfront at the Footbridge
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Single family house, over one hundred years old, accommodates ten. Three queen beds, one double bed with a trundle, and ...
From $714 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vintage Rockport Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $390 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our idyllic retreat, the ultimate vacation spot for you, your family, and friends. Nestled between the picture ...
From $279 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Oceanfront home right on Long Beach near town & whale watching with tennis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Oceanfront Cottage - Long Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $286 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Wingaerchic: A hidden retreat near Gloucester's sandy Wingaersheek Beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This very private contemporary house is perched on a shady hilltop near Gloucester's sandy Wingaersheek Beach. It's spac ...
From $409 per night (USD)VRBO
- From $707 per night (USD)
VRBO
Grand Home Between Good Harbor and Long Beach. 2 King beds, AC, outdoor shower.
- Bedrooms:
- 2
- Bathrooms:
- 8
- Sleeps:
- 16
Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your lif ...
From $707 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Sweet, Bright, Water Views & 2 min walk to Beach Discounts available see below
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and make memories of a lifetime!! Easy living open floor plan, beachy bright and steps to Cape Hedge Beach and Long ...
From $575 per night (USD)VRBO
- From $581 per night (USD)
VRBO
Fantastic Ocean Views - Text 603-801-1486 for 10% discount
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Ocean Crag has gorgeous ocean views and is located steps away from Cape Hedge and Long Beaches. Enjoy breathtaking view ...
From $581 per night (USD)VRBO
- From $857 per night (USD)
VRBO
NEW Rental: 2 min walk to Private Coffin's Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy this fantastic beach house just a quick 5 minute walk to Coffin's Beach. → Sleeps 10 → 1 King bed, 2 Twin beds, ...
From $857 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Walk to Good Harbor Beach, pet friendly, family beach home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a memorable family vacation in this fully furnished, 3 bedroom single-family home with deck, yard and marsh views, ...
From $300 per night (USD)VRBO
- From $437 per night (USD)
VRBO
Super cute cottage, steps from beautiful sandy Long Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom plus loft for kids, 2 full bathroom cottage is only a few feet from the beautiful and sandy Long Beach in ...
From $437 per night (USD)VRBO
- From $249 per night (USD)
Expedia
ROCKPORT, MA ~ The LOFT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Loft suite is located in the seaside town of Rockport, MA. Just 1.4 miles from downtown, this 1 bedroom/1 bathroom a ...
From $249 per night (USD)Expedia
- From $374 per night (USD)
VRBO
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the ...
From $374 per night (USD)VRBO
- From $540 per night (USD)
VRBO
The Haabah Beach Retreat—4 Minute Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two-bedroom gorgeous beach house overlooking Good Harbor Beach, located DIRECTLY on the Good Harbor estuary. The house i ...
From $540 per night (USD)VRBO
- From $199 per night (USD)
VRBO
VIEWS! Annisquam Bridge House at Lobster Cove.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Annisquam Bridge House-a renovated second floor unit high above Lobster Cove, Perfect getaway for a couple. It can acco ...
From $199 per night (USD)VRBO
- From $197 per night (USD)
VRBO
Sandy Bay: An oceanfront gem vacation rental with ocean views in Rockport.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to an oceanfront gem with exquisite views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short di ...
From $197 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy beautiful views of Sandy Bay and the Atlantic from this classic New England vacation rental home on Rockport's Pig ...
From $405 per night (USD)VRBO
- From $686 per night (USD)
Expedia
Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
THE HOME: This house was built in 2018 with every modern amenity and comfort for vacation life. Vaulted ceilings in the ...
From $686 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Bright and airy home in Rockport, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Our home is a Cape style Victorian era house with modern updates, hardwood floors and lots of charm. All the rooms have ...
From $225 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river an ...
From $455 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurst ...
From $375 per night (USD)VRBO
- From $208 per night (USD)
VRBO
Helena House: European flair, close to Plum Cove Beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the se ...
From $208 per night (USD)VRBO
- From $242 per night (USD)
VRBO
Granite Cottage: Charming cottage in Rockport with private deck and views.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier ...
From $242 per night (USD)VRBO
- From $256 per night (USD)
VRBO
Captain John Butman House: Charming historic home in the village of Rockport.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape H ...
From $256 per night (USD)VRBO
- From $305 per night (USD)
VRBO
You will love our location and will return for our hospitality!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
After the success of A Breezy Cottage, we set our sails on The Life of Reilly! The property was purchased in September, ...
From $305 per night (USD)VRBO
- From $610 per night (USD)
Expedia
Hidden Gem - 3 Minute Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
✔ Great location: short walk to Niles Beach ✔ 5 beds: king, queen, 3 twins (2 full baths) ✔ 3-car parking, EV charger* ✔ ...
From $610 per night (USD)Expedia
- From $223 per night (USD)
VRBO
Jewel Box: A gem of a rental home close to Good Harbor Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Situated at the end of a quiet street and down the road from Good Harbor Beach, Jewel Box is a gem of a rental home. Thi ...
From $223 per night (USD)VRBO
- Click For Pricing
Expedia
COME STAY AT THE MERMAID COTTAGE ON LANES COVE !
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The mermaid cottage is a sunny quaint cottage with a large sunny kitchen, cozy living room, and large upstairs bedroom w ...
Click For PricingExpedia
- From $281 per night (USD)
VRBO
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of s ...
From $281 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Sage Hill: Perfectly situated for Long Beach, Gloucester, and Rockport.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage ...
From $399 per night (USD)VRBO
- From $537 per night (USD)
VRBO
Granite Pier: Blends craftsmanship with modern amenities. Water views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Granite Pier, with its unparalleled ocean views, is a traditional Cape Ann home with an unusual history. Built in the mi ...
From $537 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Cozy, Waterview Old Quarryman boarding house
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Adorable 1 bedroom (with memory foam folding cot for xtra guests) Sleep Sofa. Has foma topper, High ceilings, laundry, ...
From $175 per night (USD)VRBO