A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

1. Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"A lovely place! Very clean with very comfortable beds! "
United States
Mariyana K.
The price is CA $186
CA $462 total
includes taxes & fees
Sep 23 - Sep 24
Quaint Neighborhood / Close to Beaches

2. Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (20 reviews)
"We had a very pleasant stay. Nice quiet location. Clean apartment. Great host. Would stay again. Thank you for sharing your place with us."
United States
John P.
The price is CA $220
CA $476 total
includes taxes & fees
Sep 27 - Sep 28
Charming Retreat

3. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful, wonderfully well stocked home with everything anyone would need! And not just starter supplies either! They even have beach necessities in a shed out back! Quality and quantity amazing in everything! Beautiful views, comfortable rocking chairs on front porch. Everything was great!!"
United States
Michele V.
The price is CA $267
CA $738 total
includes taxes & fees
Sep 15 - Sep 16
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

4. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Lovely, large room with beams on the ceiling and a very comfortable bed. Clean and inviting. Appreciated the detailed, friendly messages from the host. The building is near a pretty pond and the store downstairs sells coffee for a dollar!"
United States
Catherine C.
The price is CA $198
CA $295 total
includes taxes & fees
Sep 27 - Sep 28
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

5. Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (21 reviews)
"For our one night stay it was perfect, Clean and comfortable, plenty of basic's, bedding, towels and kitchen supply's."
United States
CHARLES
The price is CA $277
CA $576 total
includes taxes & fees
Sep 21 - Sep 22
Cozy two bedroom house in the heart of Gloucester

6. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is CA $375
CA $474 total
includes taxes & fees
Sep 22 - Sep 23
The Essex of Gloucester

7. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (20 reviews)
"Very clean and quaint. There is definitely noise you can hear from upstairs but not in a way that was bothersome. We enjoyed our stay!"
United States
Jessica M.
The price is CA $307
CA $600 total
includes taxes & fees
Sep 13 - Sep 14
Ocean Breeze / 8-Minute Walk to Beach

8. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (14 reviews)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
The price is CA $235
CA $615 total
includes taxes & fees
Sep 28 - Sep 29
Oceanside Village Home~Private Fenced Yard~Reserved Parking

9. Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (4 reviews)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is CA $439
CA $1,336 total
includes taxes & fees
Sep 14 - Sep 15
Classic Coastal Family Home | Walk to Sea;King Bed

10. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
10.0 out of 10, Exceptional, (17 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is CA $457
CA $950 total
includes taxes & fees
Oct 7 - Oct 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

11. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (3 reviews)
"Comfortable, clean and very much natural light. The beds are incredibly comfortable. A great place as a homebase when visiting the area."
United States
Richard B.
The price is CA $488
CA $1,279 total
includes taxes & fees
Sep 14 - Sep 15
New England Coastal Residence

12. Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Downtown Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Everything was great! Felt like I was in my own house"
United States
Bill D.
The price is CA $238
CA $557 total
includes taxes & fees
Oct 13 - Oct 14
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

13. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
10.0 out of 10, Exceptional, (1 review)
"We loved our stay. The property is beautiful with wonderful views. Convenient to get most places."
United States
Sara G.
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

14. Stay at Good Harbor Beach

Stay at Good Harbor Beach
East Gloucester
10.0 out of 10, Exceptional, (1 review)
"House was incredible and great for a group. Super nice house with everything we needed. Walked to the beach , cooked great meals, Allie was super helpful and accommodating. Would love to come back."
United States
hawley s.
The price is CA $2,241
CA $3,831 total
includes taxes & fees
Sep 21 - Sep 22
Stay at Good Harbor Beach

15. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (41 reviews)
"This is our second year staying at Gigi's place. It's such a great location and value. It offers everything we like during the off season without the crowds and is such a clean and comfortable place to stay."
United States
Victoria P.
The price is CA $160
CA $391 total
includes taxes & fees
Sep 21 - Sep 22
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

16. 1BR with Private Deck + Ocean Views· Private Parking · King Bed

1BR with Private Deck + Ocean Views· Private Parking · King Bed
Rockport
9.8 out of 10, Exceptional, (42 reviews)
"Perfect house for a stay in Rockport. Clean, well decorated and the perfect location for walking around the town and also exploring the east coast. "
United States
Leanna S.
The price is CA $172
CA $444 total
includes taxes & fees
Sep 15 - Sep 16
1BR with Private Deck + Ocean Views· Private Parking · King Bed

17. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (36 reviews)
"Very clean property located on the rock port harbor and downtown. Amazing view of the harbor. Enjoyed watching the lobster boats leaving early in the morning. Our host was very gracious and accommodating. Very walkable location with lots to do. Enjoyed our stay very much."
United States
Linda
The price is CA $174
CA $410 total
includes taxes & fees
Sep 16 - Sep 17
Harborside Oasis ★ Harbor View ★ Heart of Downtown

18. Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (220 reviews)
"Excellent above garage large studio in a superb Rockport location central to everything. Hosts were gracious and warm and made the overnight stay a good one. Highly recommend."
United States
Eugene
The price is CA $270
CA $343 total
includes taxes & fees
Sep 16 - Sep 17
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

19. Apartment with private rooftop deck with ocean views

Apartment with private rooftop deck with ocean views
Rockport
10.0 out of 10, Exceptional, (22 reviews)
"A beautiful home clean with everything we needed for our stay. We enjoyed our stay and I would definitely book again!"
United States
Ellen W.
The price is CA $242
CA $482 total
includes taxes & fees
Sep 16 - Sep 17
Apartment with private rooftop deck with ocean views

20. The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
10.0 out of 10, Exceptional, (43 reviews)
"Absolutely perfect Stay! Wonderful host and wonderful location. We will definitely be back!"
United States
Shannon R.
The price is CA $251
CA $606 total
includes taxes & fees
Sep 15 - Sep 16
The Bookstore · Private Parking · King Beds · Downtown Rockport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gloucester Hotel Reviews

Find out more about Gloucester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gloucester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Gloucester?

Yes, we offer vacation rentals in Gloucester close to Maritime Gloucester, or you can choose a more remote option if you'd like a relaxing place to stay. Visitors like the scenic seaside and waterfront in Gloucester. Make sure you have time to check out the seafood restaurants and monuments during your trip.

What are some of the best vacation rentals that Gloucester has to offer?

Peaceful centrally located home: w/ yard & walking distance to town: This Gloucester vacation home rental offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other top choices in Gloucester are Steps to Wingaersheek's Private 1.5 Mile White Dune Beach and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many vacation rentals are there in Gloucester?

Expedia has 174 vacation rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Pavilion Beach and Half Moon Beach are a couple of great spots to enjoy the outdoors. Capt Bill & Sons Whale Watch and Cape Ann Museum are other places to visit while you're in town.

What are vacation rentals like in Gloucester?

Vacation rentals are private properties you can stay in for a short or long stay in Gloucester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.