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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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Gloucester vacation rentals

A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

1. 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.
$279 nightly
The price is $312
Sep 21 - Sep 22
Total with taxes and fees
Charming Retreat
A cozy living room with a wooden ceiling, a sofa, a coffee table, and a door with glass panels.

2. 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.
$363 nightly
The price is $405
Sep 23 - Sep 24
Total with taxes and fees
Quaint Neighborhood / Close to Beaches
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

3. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (12 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.
$235 nightly
The price is $262
Sep 23 - Sep 24
Total with taxes and fees
The Essex of Gloucester
A sunset over a beach with trees and a rocky shoreline.

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.
$192 nightly
The price is $215
Sep 27 - Sep 28
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A staircase with wooden steps leading to a room with a wooden ceiling.

5. 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.
$372 nightly
The price is $416
Sep 9 - Sep 10
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

6. 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, (20 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
$363 nightly
The price is $405
Sep 21 - Sep 22
Total with taxes and fees
Cozy two bedroom house in the heart of Gloucester
A spacious living room with a large window, a sofa, a coffee table, a chair, and a TV mounted on the wall.

7. 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.
$556 nightly
The price is $621
Sep 22 - Sep 23
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
A crowded beach with people swimming and sunbathing, tents, and beach chairs.

8. 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.
$397 nightly
The price is $443
Sep 13 - Sep 14
Total with taxes and fees
Ocean Breeze / 8-Minute Walk to Beach
A wooden staircase with a railing leading to a covered deck area.

9. 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
$518 nightly
The price is $579
Sep 8 - Sep 9
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

10. 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.
$862 nightly
The price is $986
Sep 8 - Sep 9
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed
A modern staircase with wooden steps and metal railings, leading to a well-lit interior space.

11. New England Coastal Residence

New England Coastal Residence
Gloucester
9.6 out of 10, Exceptional, (4 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.
$794 nightly
The price is $887
Sep 8 - Sep 9
Total with taxes and fees
New England Coastal Residence
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

12. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (55 reviews)
$542 nightly
The price is $605
Sep 9 - Sep 10
Total with taxes and fees
Beach Life Bliss - steps to the beach
A living room with a wooden coffee table, two wine glasses, a black textured wall, a green sofa, and a door leading to a garden.

13. 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.
$637 nightly
The price is $712
Sep 26 - Sep 27
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
A waterfront property with a deck, a chair, a flag, and a view of the water and distant buildings.

14. Stay at Gloucester Harbor

Stay at Gloucester Harbor
Rocky Neck
10.0 out of 10, Exceptional, (1 review)
"We loved our time at the Gloucester House! The area was perfect, access to fun times at low tide created lifetime memories. And the yard overlooking the inlet was perfect, we spent hours playing outside and having fires at sunset. It was truly the perfect getaway for 6 adults and 3 kids. We had the best time!"
United States
Michelle N.
$1,387 nightly
The price is $1,549
Sep 9 - Sep 10
Total with taxes and fees
Stay at Gloucester Harbor
A living room with a fireplace, sofas, a TV, and wooden beams on the ceiling.

15. 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.
$2,422 nightly
The price is $2,769
Sep 8 - Sep 9
Total with taxes and fees
Stay at Good Harbor Beach
A harbor with boats docked, a pier, and houses along the shore.

16. 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.
$252 nightly
The price is $288
Sep 21 - Sep 22
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
A marina with boats docked, a clear sky, and a street with parked cars.

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
$258 nightly
The price is $295
Sep 28 - Sep 29
Total with taxes and fees
Harborside Oasis ★ Harbor View ★ Heart of Downtown
A beach with houses in the background and people engaging in various activities.

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, (219 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
$223 nightly
The price is $249
Sep 8 - Sep 9
Total with taxes and fees
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
A coastal town with houses along the shoreline, a beach, and a rocky outcrop.

19. 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.
$289 nightly
The price is $323
Sep 21 - Sep 22
Total with taxes and fees
1BR with Private Deck + Ocean Views· Private Parking · King Bed

20. 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.
$315 nightly
The price is $352
Sep 13 - Sep 14
Total with taxes and fees
Apartment with private rooftop deck with ocean views
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

Ashworth by the Sea

Ashworth by the Sea

10/10 Excellent
"Excellent service,"
Juan 1-night trip
Posted less than an hour ago
Ashworth by the Sea

Find out more about Gloucester

Everything you need to know about Gloucester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gloucester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This Gloucester vacation home rental is located near the beach and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Gloucester are Peaceful centrally located home: w/ yard & walking distance to town 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.