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From $151 per night (USD)
VRBO
Walk to the ocean, very private. Secluded, woodsy location.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We are a cozy studio in a unique setting. There is a babbling brook that runs through the property to the ocean. This wa ...
From $151 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Great Marsh House | Dog-friendly duplex in Essex with yard, deck & game room
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Great Marsh House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $546 per night (USD)
Expedia
From $75 per night (USD)
VRBO
Ocean Escape in Historic Lanesville – Steps from Lanes Cove
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Enjoy the first floor in this centrally located, clean, and bright home -- beautifully crafted and decorated, yet unpret ...
From $75 per night (USD)
VRBO
Click For Pricing
Expedia
The Quarry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Take it easy at this unique and tranquil magical getaway. What this place offers Lake view Public or shared beach access ...
Click For Pricing
Expedia
From $225 per night (USD)
VRBO
Centrally located charmer with expansive patio, board games, & central AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bianca's House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $225 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Cozy two bedroom house in the heart of Gloucester
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Keep it simple at this peaceful and centrally located place. This two-bedroom house is just what you need for a family, ...
From $251 per night (USD)
Expedia
From $666 per night (USD)
VRBO
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Spectacular, furnished 2-bedroom apartment is just moments from the North Shore's iconic Good Harbor Beach, Bass Rocks G ...
From $666 per night (USD)
VRBO
From $1071 per night (USD)
Expedia
Modern oceanfront home with scenic deck, grill, games, chef's kitchen, & W/D
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Magnolia Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1071 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Brand new oceanfront home with a grill, deck, & beach access - stellar views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Robbins Island Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $570 per night (USD)
VRBO
From $651 per night (USD)
VRBO
All-Season Beach Haven - walk to two beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you don't know Gloucester, a stay at our Beach Haven is the best way to experience it - and if you do know it, you'll ...
From $651 per night (USD)
VRBO
From $1477 per night (USD)
VRBO
Salt Marsh Cottage: Access to Coffins Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Salt Marsh is a large and comfortable vacation home with lush views that stretch across Farm Creek Marsh. This property ...
From $1477 per night (USD)
VRBO
From $1210 per night (USD)
VRBO
The Captain’s Villa Beachfront House With Access To Pavilion's Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Enjoy a luxury experience at this centrally located beachfront home with sweeping water views of Gloucester Harbor.The h ...
From $1210 per night (USD)
VRBO
From $406 per night (USD)
VRBO
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy seaside elegance steps to Niles Beach and Rocky Neck at The Mariner. This charming, spacious rental is also close ...
From $406 per night (USD)
VRBO
$\Captain's Lookout\ on Wonson Cove, Rocky Neck - Gloucester$
From $234 per night (USD)
Expedia
\"Captain's Lookout\" 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> <i>Quick Note: We have a two night mini ...
From $234 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Charming Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ideal for up to four people, this apartment is located on the first floor of a two-unit building. It has two bedrooms, o ...
From $243 per night (USD)
VRBO
From $689 per night (USD)
Expedia
5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This historic home has great access to one of the best hidden gems of Gloucester, Stage Fort Park. Just a five minute wa ...
From $689 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Gloucester Home w/ Large Yard: 1 Mi to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Seeking your next coastal adventure in New England? You’ll love this charming 2-bedroom, 2-bath vacation rental in Glouc ...
From $367 per night (USD)
VRBO
$NEW \Tranquil Seas\ Rockport SUMMER Rental - Convenience, Comfort and Charm$
From $398 per night (USD)
VRBO
NEW \"Tranquil Seas\" Rockport SUMMER Rental - Convenience, Comfort and Charm
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This meticulous, cozy, air conditioned home requires nothing but your suitcase and the desire to relax and have fun. Par ...
From $398 per night (USD)
VRBO
From $421 per night (USD)
VRBO
2BR/2BA Harborside Home · Fenced Backyard · Ocean View ·Walk to Rocky Neck+Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
. - Sunny and cheerful home with direct views of harbor, boating activity & glorious sunsets from your private deck & li ...
From $421 per night (USD)
VRBO
Click For Pricing
Expedia
NEW Seaside Cottage Steps from the beach + Parking + Theater
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to a serene, newly-renovated cottage located just moments from both Front and Back Beach in Rockport. This cozy f ...
Click For Pricing
Expedia
From $372 per night (USD)
VRBO
The Buoys Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Take it easy at this unique and tranquil getaway. Located less than 3 miles from beautiful beaches, popular parks and lo ...
From $372 per night (USD)
VRBO
From $572 per night (USD)
VRBO
Magnolia By The Sea-Attractive home, large yard & deck. Walk to Magnolia Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Enjoy the wooded setting, beautiful gardens and privacy of our family vacation home. Our 4 bedroom, 2 bathroom home incl ...
From $572 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Take a much-needed break from your day-to-day and book a stay at this 2-bed, 1-bath Gloucester vacation rental! Convenie ...
From $205 per night (USD)
VRBO
From $862 per night (USD)
Expedia
An oceanfront gem with exquisite views, close to downtown Rockport.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy sweeping views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short distance from Rockport village ...
From $862 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Victorian home, family and pet friendly close to beaches, harbor, restaurants
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in the East Gloucester Square Historic District this charming Victorian is in ideal proximity to all the beauty ...
From $596 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Just For The Halibut: A Northern Rockport Gem
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just For the Halibut is a charming three-bedroom, one and half bathroom house nestled between Rockport's Folly Cove and ...
From $506 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Gloucester, MA. LARGE 2 room studio with deck, Fully Furnished on a quiet street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in a serene, private, and quiet dead-end street, this delightful space in Gloucester Massachusetts, offers a per ...
From $205 per night (USD)
VRBO
Click For Pricing
Expedia
Stay at Lighthouse Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: ✔ Short 8 min stroll to Lighthouse Beach ✔ Private, peaceful wooded setting in magical Annisquam ✔ 5 comfy beds ...
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Expedia
From $569 per night (USD)
VRBO
Pool open for the season! Single family home, 5-Min walk to Good Harbor Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Be the first to stay at the newly renovated Twin Shores Poolside Haven! Escape to this charming 3-bedroom, 2-bath home ...
From $569 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Updated 1 br steps to downtown, 3 beaches, Stacey Blvd, + Stage Fort Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This unit is in a great location right in the heart of things across from Gloucester Harbor. Short walk to Half Moon, Pa ...
From $233 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Centrally located open concept apartment with parking, central AC, & W/D
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Paula's Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $344 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This charming seaside cottage is newly renovated with lots of modern conveniences and plenty of original character. You' ...
From $280 per night (USD)
Expedia
From $997 per night (USD)
VRBO
Driftwood Long Beach
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Welcome to Your Seaside Escape in Rockport, MA! Nestled along the pristine shores of Long Beach, our beach house invite ...
From $997 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Beachmont: 3 bedroom house near beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just 1/3 of a mile from Good Harbor Beach in East Gloucester! Enjoy a relaxing beach getaway in Historic Gloucester, MA. ...
From $410 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Plum Cove Beach Paradise. Overlook Plum Cove from your kitchen n only steps away
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in the Lanesville section of Gloucester, nestled just above Plum Cove Beach which beckons from the kitchen w ...
From $557 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Peaceful centrally located home: w/ yard & walking distance to town
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Gloucester Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $330 per night (USD)
Expedia
From $1139 per night (USD)
VRBO
Stay at Good Harbor Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Summary: ✔ Just a 2-minute walk to the renowned Good Harbor Beach ✔ Expansive home featuring 1 King, 2 Queens, 2 Fulls, ...
From $1139 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Blue Magnolia - A quiet apartment in a quaint Gloucester MA village
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Gloucester at this charming apartment. With 2 bedrooms, including a king bed and a queen bed ...
From $274 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Single-level living in Rockport, walk to Long Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Escape to this charming 3-bedroom vacation home, nestled among the trees with ocean views. Step out onto the spacious de ...
From $486 per night (USD)
VRBO
From $1424 per night (USD)
Expedia
Niles Beach House - Beach & Boston Skyline Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Take in the amazing view of Gloucester Harbor and the Boston skyline from this modern, fully air conditioned vacation re ...
From $1424 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Rockport Cottage w/ Patio - Steps to Beach!
Bedrooms:
1
Bathrooms:
5
Sleeps:
11
Gather your crew and escape to the gorgeous shores of Massachusetts when you stay at this charming 5-bedroom, 1.5-bathro ...
From $444 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Rockport Retreat: 1 Mi to Halibut Point State Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just steps from the sandy shores and nautical adventures in Rockport, MA, this 1-bedroom, 1-bathroom vacation rental is ...
From $210 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Stroll to SeaView/Beach; Great Yard
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
The Ledge House is an idyllic retreat nestled in the heart of Gloucester's charming Bay View village. The historic farmh ...
From $433 per night (USD)
VRBO
From $860 per night (USD)
Expedia
Maids Quarters; private beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This simple and quiet home is behind a Victorian mansion and was used as the Maid's quarters to house staff. It's now a ...
From $860 per night (USD)
Expedia
From $1200 per night (USD)
VRBO
Elegant Victorian & Quarters
Bedrooms:
3
Bathrooms:
8
Sleeps:
16
A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the color ...
From $1200 per night (USD)
VRBO
From $2598 per night (USD)
Expedia
Marina View, Walk to Niles Beach & Rocky Neck
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Springtime photos are on the way!! Take it easy at this unique and tranquil getaway in front of Smith Marina. The condo ...
From $2598 per night (USD)
Expedia
From $1098 per night (USD)
VRBO
One of a kind ocean front property - private section of Wingaersheek Beach.
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
This property offers stunning views from every vantage point of Coffin's Beach, Crane Beach, the New Hampshire and Main ...
From $1098 per night (USD)
VRBO
From $708 per night (USD)
Expedia
Cape Hedge House - Gorgeous Water Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to Cape Hedge House overlooking Saratoga Creek, Long Beach and Cape Hedge Beach in Rockport! Enjoy the soothing s ...
From $708 per night (USD)
Expedia
From $1841 per night (USD)
VRBO
Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach
Bedrooms:
6
Bathrooms:
11
Sleeps:
26
Welcome to your ultimate coastal escape at this magnificent, fully-renovated brick mansion on Eastern Point in Glouceste ...
From $1841 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Airstream & Ocean View: Unique Gloucester Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
5 Acres | Close to Beaches & Trails | Pet Friendly (w/ Fee) | Apartment + Airstream 'Glamping' with a modern twist, thi ...
From $259 per night (USD)
Expedia
From $661 per night (USD)
VRBO
The Gallery: Rocky Neck Waterfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Please note that The Gallery has a one month (31 night) minimum rental period. Welcome to The Gallery, a stunning water ...
From $661 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Portside Glimpse: Peekaboo Views of Front Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get away to this modern one-bedroom apartment located in the heart of downtown Rockport. Portside Glimpse is a bright an ...
From $434 per night (USD)
Expedia
From $630 per night (USD)
VRBO
Oceanfront Dock Escape ~ Kayaks & Paddleboards
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, M ...
From $630 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Beautifully renovated home walk to boulevard, town & train
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Longview House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $378 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Portside Overlook: Village and Beach Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Get away to this modern two-bedroom apartment located in the heart of downtown Rockport. With ocean views and decks on t ...
From $582 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Painter's Perch: Rocky Neck
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Sitting high above Rocky Neck, Painter’s Perch offers stunning views of the Neck and picturesque Smith Cove. This charmi ...
From $533 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Elegant Bayview Victorian Home; walk to beach
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spa ...
From $700 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious oceanfront 4-bed/4ba home in Gloucester with central AC & WiFi,
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Consider this house your sea side home away from home while you visit Gloucester. This delightful oceanfront property bo ...
Click For Pricing
Expedia
From $471 per night (USD)
VRBO
Stay at Little River
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Summary: ✔ Nestled along picturesque Little River ✔ Sleeps 7 with 1 King, 1 Queen, and 3 Twins ✔ Private dock for swimmi ...
From $471 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Wingaersheek, Private and Public Beach Luxury Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This home is perfectly located a few steps from the beach with an a rooftop with outstanding water views. The house is ...
From $182 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Nestled in the Rocky Neck waterfront, this updated apartment boasts 2 bedrooms - one with a queen bed and the other day ...
From $391 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Walk to DNTN/Beach/Beauport, Boat Island, New Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Captain's Quarters! This charming retreat in Gloucester, Massachusetts, features three cozy bedrooms, eac ...
From $467 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Stay at Rocky Neck Su
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: Rare Gloucester Waterfront Retreat! ✓ Perched directly on the water with breathtaking ocean views ✓ Large dec ...
From $551 per night (USD)
VRBO
From $364 per night (USD)
Expedia
New Design - Walk to DNTN, Beauport, Beach, Train
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Crows Nest! This is your perfect retreat in Gloucester, Massachusetts! This quaint home offers a cozy bed ...
From $364 per night (USD)
Expedia
From $615 per night (USD)
VRBO
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
KEY FEATURES: ☆Entire 2 story fully renovated home that sleeps 8 adults comfortably ☆Private backyard with a gas grill a ...
From $615 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Mill Brook House: The Best of Rockport
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in the heart of historic Rockport, Mill Brook House beautifully blends timeless charm with modern conveniences. ...
From $604 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Coastal Comfort—Walk to Beach & Cafés
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This spacious 3-bedroom home sleeps six and features two kitchens, hardwood floors, and smart TVs. The first-fl ...
From $570 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Refreshing Ocean and Sunset View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this homey 3-bedroom retreat in Lanesville. Just a 5-minute walk to the ocean, where waves crash on massive bo ...
From $495 per night (USD)
Expedia
From $956 per night (USD)
VRBO
Beach Front Gem on Coffin's -Wingaersheek Beach - Gloucester, MA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gloucester is waiting for you at this 3-bedroom beach front home. Relax with the whole family at this beautiful three be ...
From $956 per night (USD)
VRBO
From $1724 per night (USD)
VRBO
Oceanfront Castle on 40 Acres - 10 bedrooms, AC, & WiFi in Manchester-by-the-Sea
Bedrooms:
5
Bathrooms:
10
Sleeps:
20
We offer the perfect retreat for you and yours. The Sharksmouth Estate is a private family-owned 40-acre woodland and oc ...
From $1724 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Life of Reilly - Private & Serene Rockport Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New for Summer 2025! Life of Reilly is a stylish 2-bedroom, 1.5-bathroom vacation home tucked away on a serene 4.5-acre ...
From $446 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Tranquil Beachfront 2-bedroom townhome in charming Gloucester with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Steps to Long Beach Gloucester with this soothing condo offering heating, AC, a washing machine, WiFi, and an iron. With ...
From $475 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Charming Waterfront 1 bedroom apartment in wonderful E. Gloucester with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a peaceful stay at this delightful 1-bedroom apartment in RockyNeck, Gloucester. The cozy bedroom features 1 full ...
From $309 per night (USD)
VRBO
From $794 per night (USD)
Expedia
Oceanfront Cottage next to Lighthouse, sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to this charming 4-bedroom cottage, offering breathtaking ocean views and the ultimate coastal retreat. Ideal for ...
From $794 per night (USD)
Expedia
From $427 per night (USD)
VRBO
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY FEATURES: * 2 story townhouse that sleeps 8 comfortably * Walking distance to beaches and Downtown Gloucester *Fully ...
From $427 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Oceanfront Luxury 3BR Townhome, 9-Month School Year Rental in Gloucester
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
End of August 2025 to May 2026 Rental. Academic Year Oceanfront Rental in Gloucester, Massachusetts—Ideal for Parents, ...
From $503 per night (USD)
Expedia
From $1796 per night (USD)
VRBO
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
Bedrooms:
7
Bathrooms:
9
Sleeps:
24
*MORE PHOTOS COMING SOON ☀ Sleeps 24 guests across 9 bedrooms ☀ Perched on the Back Shore ~ 1 mile or 5min drive to Good ...
From $1796 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Tidebend: River views and gracious comfort
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annis ...
From $736 per night (USD)
Expedia
From $499 per night (USD)
VRBO
River view home w/ deck, river access, near beaches and train
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Little River Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $499 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Stay at Smith Cove: Rare Gloucester Waterfront Retreat
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Rare Gloucester Waterfront Retreat! ✓ Nestled above the scenic Smith Cove in Rocky Neck with breathtaking harbor views ...
From $459 per night (USD)
Expedia
$\nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.$
From $377 per night (USD)
VRBO
\nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax in the soothing ambiance after a day of exploring some of our fine restaurants and shops among other fine attract ...
From $377 per night (USD)
VRBO
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Expedia
Charming 2nd floor apartment on Lane's Cove
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our charming oceanside apartment in the picturesque village of Lanesville is perfectly situated on the edge of Lanes Cov ...
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Expedia
From $388 per night (USD)
VRBO
Charming bungalow with pool! Walk to Front Beach and shops! Sep-Oct Availability
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We are the delighted new owners of this well established & well loved short term rental! This Rockport bungalow sits on ...
From $388 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Close to Good Harbor Beach, 3 bedroom apartment
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Located in a quiet neighborhood within a half mile of Good Harbor Beach, relax and enjoy the beauty of Gloucester. The ...
From $392 per night (USD)
VRBO
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VRBO
Harbor Lights: Charming 5-Bedroom Seaside Cottage in East Gloucester
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Forget your worries at Harbor Lights. Listen to the waves crash on Niles Beach from a rocking chair on the enormous scre ...
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VRBO
From $475 per night (USD)
Expedia
Stay at The Neck: Nautical Charm Meets Waterfront Living
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Nautical Charm Meets Waterfront Living: Vintage Sailboat-Inspired Home ✓ Perched above Smith Cove with sweeping views o ...
From $475 per night (USD)
Expedia
From $454 per night (USD)
VRBO
cottage close to long beach and good harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summer at its best! A delightful spot near the beach with nice private backyard, walkable to Long Beach and Good Harbor ...
From $454 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Spacious Retreat Near Good Harbor Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Just a quick 15-minute walk to the Little Good Harbor footbridge, this spacious 4-bedroom home sleeps 10 and fe ...
From $609 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Spy Glass - Views of Ipswich Bay
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
New for 2025! Perched on the third floor of a well-maintained building, this modern two-bedroom apartment offers comfort ...
From $310 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Lovely 5-bedroom cottage in Gloucester
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
On the ocean’s edge, this peaceful, rustic retreat, once a 1920s girls camp, now a beloved family home, is the perfect s ...
From $642 per night (USD)
Expedia

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Results: 290 Rentals