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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Gloucester vacation rentals

A crowded beach with people swimming and sunbathing, tents, and beach chairs.

1. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (21 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.
$291 nightly
The price is $325
Oct 15 - Oct 16
Total with taxes and fees
Ocean Breeze / 8-Minute Walk to Beach
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

2. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (57 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
$320 nightly
The price is $357
Oct 20 - Oct 21
Total with taxes and fees
Beach Life Bliss - steps to the beach
A sunset over a beach with trees and a rocky shoreline.

3. 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, (3 reviews)
"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.
$208 nightly
The price is $232
Oct 29 - Oct 30
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

4. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (22 reviews)
"Parking was great...easy access to visiting all of Cape Ann"
United States
Margaret
$320 nightly
The price is $358
Oct 6 - Oct 7
Total with taxes and fees
Charming Retreat
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.

5. 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.
$407 nightly
The price is $454
Oct 13 - Oct 14
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

6. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 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.
$299 nightly
The price is $334
Oct 27 - Oct 28
Total with taxes and fees
The Essex of Gloucester
A kitchen with white cabinets, a dining table with chairs, and a hanging light fixture.

7. The Duval House

The Duval House
Downtown Gloucester
9.4 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay. The house was very nice and the room was very clean. Can’t wait to come back!"
United States
Jennifer H.
$455 nightly
The price is $508
Oct 21 - Oct 22
Total with taxes and fees
The Duval House
A wooden staircase with a railing leading to a covered deck area.

8. 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
9.8 out of 10, Exceptional, (20 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
$567 nightly
The price is $633
Oct 7 - Oct 8
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A cozy living room with a wooden ceiling, a sofa, a coffee table, and a door with glass panels.

9. 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.
$405 nightly
The price is $453
Oct 15 - Oct 16
Total with taxes and fees
Quaint Neighborhood / Close to Beaches
Interior

10. Luxury Starboard Townhome Steps to Niles Beach

Luxury Starboard Townhome Steps to Niles Beach
East Gloucester
$1,153 nightly
The price is $1,320
Oct 13 - Oct 14
Total with taxes and fees
Luxury Starboard Townhome Steps to Niles Beach
A staircase with wooden steps leading to a room with a wooden ceiling.

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (15 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.
$423 nightly
The price is $472
Nov 2 - Nov 3
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

12. 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, (5 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.
$940 nightly
The price is $1,075
Oct 6 - Oct 7
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.

13. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 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.
$804 nightly
The price is $898
Oct 5 - Oct 6
Total with taxes and fees
New England Coastal Residence
A bedroom with a bed, bedside tables, a desk, and a bench.

14. 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.
$606 nightly
The price is $677
Oct 26 - Oct 27
Total with taxes and fees
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
A spacious living room with a large TV, comfortable seating, and large windows offering a view of the outdoors.

15. Stay at Little River

Stay at Little River
Gloucester
10.0 out of 10, Exceptional, (9 reviews)
"My friend and I had a great time staying at the house. Beautiful view, close to great attractions, and the kitchen was well appointed."
United States
Caitlin D.
$1,026 nightly
The price is $1,146
Oct 15 - Oct 16
Total with taxes and fees
Stay at Little River
A waterfront property with a dock, a small house with a balcony, and a larger house with a garage.

16. 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
A room with two sofas facing a central table, large windows with wooden frames, and a chandelier.

17. Edgemoor Estate - 11 Bed/6.5 Bath l Sleeps 32 - Pool, Hot Tub, Walk to Beach

Edgemoor Estate - 11 Bed/6.5 Bath l Sleeps 32 - Pool, Hot Tub, Walk to Beach
East Gloucester
$3,112 nightly
The price is $3,560
Oct 6 - Oct 7
Total with taxes and fees
Edgemoor Estate - 11 Bed/6.5 Bath l Sleeps 32 - Pool, Hot Tub, Walk to Beach
A harbor with boats docked, a pier, and houses along the shore.

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

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (43 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
Oct 5 - Oct 6
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
A beach with houses in the background and people engaging in various activities.

19. 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, (222 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
Oct 15 - Oct 16
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.

20. Downtown Rockport · King Bed w/Parking · Walk to Train

Downtown Rockport · King Bed w/Parking · Walk to Train
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
Oct 5 - Oct 6
Total with taxes and fees
Downtown Rockport · King Bed w/Parking · Walk to Train
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

The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

10/10 Excellent
"Clean room, convenient parking, very nice stay."
JENNIE 3-night trip
Posted 6 hours ago
The Wylie Inn and Conference Center at Endicott College

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 $217 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?

Beach Life Bliss - steps to the beach: This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Gloucester are Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and Single Level Home - Steps to Downtown Gloucester & A/C throughout .

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 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.