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Gloucester Rentals

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From $269 per night (USD)
VRBO
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 $269 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $353 per night (USD)
VRBO
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 $353 per night (USD)
VRBO
From $591 per night (USD)
Expedia
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 $591 per night (USD)
Expedia
From $357 per night (USD)
VRBO
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 $357 per night (USD)
VRBO
From $587 per night (USD)
Expedia
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 $587 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $369 per night (USD)
Expedia
Stay at Little River
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Summary: ✔ Waterfront Location – Nestled on picturesque Little River with peaceful views ✔ Sleeps 7 – 1 King • 1 Queen • ...
From $369 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 $474 per night (USD)
Expedia
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 ✓ Expansive ...
From $474 per night (USD)
Expedia
From $421 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 $421 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Mill Brook House: A Colonial Original
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in the heart of historic Rockport, Mill Brook House beautifully blends timeless charm with modern conveniences. ...
From $581 per night (USD)
Expedia
From $436 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 $436 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $390 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 $390 per night (USD)
VRBO
From $1814 per night (USD)
Expedia
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 $1814 per night (USD)
Expedia
From $738 per night (USD)
VRBO
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 $738 per night (USD)
VRBO
From $499 per night (USD)
Expedia
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)
Expedia
From $457 per night (USD)
VRBO
Stay at Smith Cove Su
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Summary: Rare Gloucester Waterfront Retreat! ✓ Rocky Neck Location – Nestled above scenic Smith Cove with breathtaking ...
From $457 per night (USD)
VRBO
$\nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.$
From $376 per night (USD)
Expedia
\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 $376 per night (USD)
Expedia
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VRBO
Charming 2nd floor apartment on Lane's Cove
Bedrooms:
1
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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VRBO
From $449 per night (USD)
Expedia
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 $449 per night (USD)
Expedia
From $358 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 $358 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Stay at The Neck Summ
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: ✓ Smith Cove Views – Perched above the harbor with sweeping water & neighborhood scenery ✓ Two Spacious Decks – ...
From $439 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 $500 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 $500 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 $312 per night (USD)
Expedia
Stay at East Gloucester
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Summary: Charming East Gloucester Home ✓ Prime Location – Walk to beaches, parks & local attractions ✓ Outdoor Retreat ...
From $312 per night (USD)
Expedia
From $1253 per night (USD)
VRBO
Bell View: Private tennis court and an in-law
Bedrooms:
5
Bathrooms:
6
Sleeps:
17
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate u ...
From $1253 per night (USD)
VRBO
From $1424 per night (USD)
VRBO
Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck
Bedrooms:
3
Bathrooms:
7
Sleeps:
18
Escape to this beautiful Home nestled in the heart of Rocky Neck. This home boasts newly renovated interiors adorned wit ...
From $1424 per night (USD)
VRBO
From $340 per night (USD)
VRBO
Canal Water View; Steps to Ocean, Boulevard, Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your charming waterfront retreat in central downtown Gloucester! This delightful 2-bedroom, 1-bathroom apartm ...
From $340 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Guest House on Private Estate with Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to this charming Gloucester home! This delightful 2-bedroom, 1-bath guest home is perfect for families. Enjoy a ...
From $383 per night (USD)
Expedia

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Gloucester Rentals

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Results: 232 Rentals

Airstream & Ocean View: Unique Gloucester Getaway

The Gallery: Rocky Neck Waterfront

Portside Glimpse: Peekaboo Views of Front Beach

Oceanfront Dock Escape ~ Kayaks & Paddleboards

Beautifully renovated home walk to boulevard, town & train

Portside Overlook: Village and Beach Views!

Painter's Perch: Rocky Neck

Stay at Little River

Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries

Stay at Rocky Neck Su

4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Mill Brook House: A Colonial Original

Life of Reilly - Private & Serene Rockport Escape

Charming Waterfront 1 bedroom apartment in wonderful E. Gloucester with WiFi, AC

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Tidebend: River views and gracious comfort

River view home w/ deck, river access, near beaches and train

Stay at Smith Cove Su

\nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.

Charming 2nd floor apartment on Lane's Cove

Charming bungalow with pool! Walk to Front Beach and shops! Sep-Oct Availability

Close to Good Harbor Beach, 3 bedroom apartment

Stay at The Neck Summ

cottage close to long beach and good harbor

Spacious Retreat Near Good Harbor Beach

Spy Glass - Views of Ipswich Bay

Stay at East Gloucester

Bell View: Private tennis court and an in-law

Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck

Canal Water View; Steps to Ocean, Boulevard, Park

Guest House on Private Estate with Beach