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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Gloucester vacation rentals

Smart TV, books

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.
$302 nightly
The price is $337
Sep 29 - Sep 30
Total with taxes and fees
Quaint Neighborhood / Close to Beaches
Smart TV, fireplace

2. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (21 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.
$274 nightly
The price is $306
Sep 27 - Sep 28
Total with taxes and fees
Charming Retreat
Smart TV, books

3. 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
$363 nightly
The price is $405
Sep 21 - Sep 22
Total with taxes and fees
Cozy two bedroom house in the heart of Gloucester
Interior

4. 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.
$367 nightly
The price is $410
Oct 13 - Oct 14
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Beach

5. 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.
$182 nightly
The price is $203
Sep 27 - Sep 28
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Smart TV, books

6. 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.
$517 nightly
The price is $577
Sep 22 - Sep 23
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Property grounds

7. 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, (18 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
$544 nightly
The price is $607
Sep 17 - Sep 18
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Sun loungers, beach towels

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.
$359 nightly
The price is $401
Oct 15 - Oct 16
Total with taxes and fees
Ocean Breeze / 8-Minute Walk to Beach
Private kitchen

9. 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.
$183 nightly
The price is $204
Sep 17 - Sep 18
Total with taxes and fees
The Essex of Gloucester
Interior

10. 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.
$398 nightly
The price is $444
Sep 28 - Sep 29
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Exterior

11. 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.
$900 nightly
The price is $1,028
Sep 21 - Sep 22
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed
Interior

12. 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.
$827 nightly
The price is $924
Sep 21 - Sep 22
Total with taxes and fees
New England Coastal Residence
Exterior

13. Stay at Rocky Neck

Stay at Rocky Neck
Rocky Neck
10.0 out of 10, Exceptional, (15 reviews)
"Our host was amazing and this was the perfect getaway for us in a beautiful location!"
United States
Joy B.
$1,519 nightly
The price is $1,697
Oct 12 - Oct 13
Total with taxes and fees
Stay at Rocky Neck
Marina

14. 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.
$247 nightly
The price is $282
Sep 21 - Sep 22
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Beach nearby, sun loungers, beach towels

15. 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
$222 nightly
The price is $248
Sep 20 - Sep 21
Total with taxes and fees
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Beach

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.
$277 nightly
The price is $309
Sep 21 - Sep 22
Total with taxes and fees
1BR with Private Deck + Ocean Views· Private Parking · King Bed
Property grounds

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
$259 nightly
The price is $296
Sep 28 - Sep 29
Total with taxes and fees
Harborside Oasis ★ Harbor View ★ Heart of Downtown
Outdoor dining

18. 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.
$285 nightly
The price is $318
Sep 20 - Sep 21
Total with taxes and fees
Apartment with private rooftop deck with ocean views
Marina

19. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (44 reviews)
"Our family of four humans and two tiny dogs enjoyed our stay at this cozy home. The neighborhood is cute, quiet, and perfectly located to get in and out of town easily. The high appliances made cooking, laundry, and dishes convenient. We‘d love to stay here again."
United States
Bridget H.
$433 nightly
The price is $484
Sep 17 - Sep 18
Total with taxes and fees
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Interior

20. Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!

Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
Rockport
10.0 out of 10, Exceptional, (11 reviews)
"Great place near center of town. Cozy accommodations. Great communication with host."
United States
Kara G.
$408 nightly
The price is $456
Oct 13 - Oct 14
Total with taxes and fees
Quaint & Cozy Rockport Gem ~ Walk to Sea ~ BBQ & Private Parking!
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

Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

8/10 Good
"I"
Ray 1-night trip
Posted 1 hour ago
Holiday Inn Hotel & Suites Boston - Peabody by IHG

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 $198 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 175 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 Half Moon Beach and Stage Fort Park 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.