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Gloucester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Gloucester vacation rentals

Full-size fridge, microwave, oven, stovetop
Long Beach Suites

Aparthotel in East Gloucester

Long Beach Suites
2.0 star property
9.2 out of 10, Wonderful, (60)
"Beautiful clean and spacious condo right near long beach in Gloucester. The property management company is friendly and is very responsive. The room I had was newly renovated. It had 2 big smart tvs and a fully stocked kitchen. The keypad door lock is nice as well. I'd definitely stay here again the next time I'm in Gloucester. There's plenty of restaurants and even a shaws right up the road. George's is a great restaurant/cafe up the street with great service and food."
United States
Alexander
Long Beach Suites
Private kitchen
New Design - Walk to DNTN, Beauport, Beach, Train

Apartment in Downtown Gloucester

New Design - Walk to DNTN, Beauport, Beach, Train
10.0 out of 10, Exceptional, (3)
"Absolutely charming place! It’s had all the essentials for a weekend stay and look forward to coming back soon. Darryl was on top of communication. Thanks again! "
United States
Christine D.
The price is ￥15,171
￥51,262 total
includes taxes & fees
Dec 26 - Dec 27
New Design - Walk to DNTN, Beauport, Beach, Train
Beach
Long Beach Suites: Ocean Views, Book 2025 Already!

Apartment in East Gloucester

Long Beach Suites: Ocean Views, Book 2025 Already!
9.2 out of 10, Wonderful, (21)
"The location was perfect- couldn't have been any better. Clean and stocked kitchen. Great communication. Really enjoyed our stay here!!"
United States
Alex R.
The price is ￥18,266
￥54,497 total
includes taxes & fees
Dec 26 - Dec 27
Long Beach Suites: Ocean Views, Book 2025 Already!
Private kitchen
The Essex of Gloucester

Vacation Home in Gloucester

The Essex of Gloucester
2.0 star property
The price is ￥22,455
￥28,566 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Essex of Gloucester
Outdoor dining
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Vacation Home in Gloucester

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
9.8 out of 10, Exceptional, (11)
"We loved cooking on the antique stove and hanging out in the sun room. It was a cozy spot close to all the activities in Rockport."
United States
Allyson Y.
The price is ￥19,009
￥59,726 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Smart TV, fireplace
2BR Historic Marblehead Home+Minutes to Beach

Vacation Home in Marblehead

2BR Historic Marblehead Home+Minutes to Beach
2.0 star property
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
The price is ￥20,506
￥61,619 total
includes taxes & fees
Dec 31 - Jan 1, 2026
2BR Historic Marblehead Home+Minutes to Beach
Smart TV, books
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Vacation Home in Rockport

The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
2.0 star property
9.8 out of 10, Exceptional, (7)
"We had a great stay! Perfect location and a great setup for our family. Beautiful outdoor area and we were lucky with the weather! "
United States
Matt T.
The price is ￥20,139
￥60,686 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
Apartment (1 Bedroom) | Interior
1 Mi to Downtown: Salem Vacation Rental!

Apartment in Salem

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great overall stay! "
United States
Tessa
The price is ￥18,089
￥51,421 total
includes taxes & fees
Dec 28 - Dec 29
1 Mi to Downtown: Salem Vacation Rental!
Fridge, microwave, oven, stovetop
Harborside Oasis ★ Harbor View ★ Heart of Downtown

Apartment in Rockport

Harborside Oasis ★ Harbor View ★ Heart of Downtown
10.0 out of 10, Exceptional, (22)
"good location"
United States
Bruce S.
Harborside Oasis ★ Harbor View ★ Heart of Downtown
TV
Comfy King Beds~5 min to Salem

Apartment in Beverly

Comfy King Beds~5 min to Salem
10.0 out of 10, Exceptional, (2)
"Lovely second floor apartment! Great for a pet too. Lovely pet friendly small beach side park 8 minute walk away. Great place to stay if you’re looking to visit Salem "
United States
Jaylee G.
The price is ￥17,798
￥37,237 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Comfy King Beds~5 min to Salem
Lake
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Vacation Home in Ipswich

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
9.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
United States
Amanda A.
The price is ￥15,438
￥35,068 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Outdoor dining
1BR with Private Deck + Ocean Views· Private Parking · King Bed

Apartment in Rockport

1BR with Private Deck + Ocean Views· Private Parking · King Bed
9.8 out of 10, Exceptional, (34)
"Nice place, great location. Short walk to restaurants and sights. "
United States
Kathryn
The price is ￥13,130
￥38,034 total
includes taxes & fees
Dec 29 - Dec 30
1BR with Private Deck + Ocean Views· Private Parking · King Bed
Beach nearby, sun loungers
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Vacation Home in Rockport

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
2.0 star property
10.0 out of 10, Exceptional, (35)
"Everything about our stay was perfect ! The house, its location to the beaches, town and the idyllic Millbrook Meadow Park. The check in was seamless, the house was very clean and had everything we needed. We are definitely going back! "
United States
Tammi M.
The price is ￥21,982
￥63,616 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Property grounds
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Apartment in Rockport

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
9.8 out of 10, Exceptional, (29)
"Great place for the two of us, centrally located and met all of our expectations."
United States
Charles S.
The price is ￥14,736
￥38,408 total
includes taxes & fees
Dec 28 - Dec 29
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Beach
Swampscott! Walk Dtwn and beach

Apartment in Swampscott

Swampscott! Walk Dtwn and beach
10.0 out of 10, Exceptional, (3)
"Great spot!"
United States
William
The price is ￥14,363
￥35,790 total
includes taxes & fees
Dec 29 - Dec 30
Swampscott! Walk Dtwn and beach
Fridge, microwave, oven, stovetop
Dusk Suite at The Hygge House, Dusk Suite at The Hygge House

Apartment in Newburyport

Dusk Suite at The Hygge House, Dusk Suite at The Hygge House
2.0 star property
8.6 out of 10, Excellent, (4)
"The room was nice, there should have been 4 towels instead of just 2 and an extra blanket as just the sheet and bedspread were thin for cold nights. We did see staff in the morning and got another blanket they were very nice. Parking was tough. "
United States
Jill T.
The price is ￥12,577
￥26,122 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Dusk Suite at The Hygge House, Dusk Suite at The Hygge House
Interior
Oceanfront Oasis | 2BR Monthly | Salisbury

Condo in Salisbury Beach

Oceanfront Oasis | 2BR Monthly | Salisbury
9.8 out of 10, Exceptional, (34)
"Great location! Beds were super comfortable. Host very responsive. Highly recommend. "
United States
Katie M.
The price is ￥18,713
￥58,701 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Oceanfront Oasis | 2BR Monthly | Salisbury
Exterior
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

Condo in Beverly

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
10.0 out of 10, Exceptional, (32)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
The price is ￥16,218
￥45,638 total
includes taxes & fees
Dec 29 - Dec 30
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
Fridge, microwave, oven, stovetop
3B apt Downtown Ipswich

Apartment in Ipswich

3B apt Downtown Ipswich
10.0 out of 10, Exceptional, (13)
"Clean, close to everything, great stay"
United States
Jeff P.
3B apt Downtown Ipswich
Marina
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Condo in Marblehead

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (71)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
The price is ￥16,062
￥41,805 total
includes taxes & fees
Dec 29 - Dec 30
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead 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

The Cove At Salem

The Cove At Salem

10/10 Excellent
"Everything was good! I even figured how to use the tv!"
Henry 1-night trip
Posted 2 days ago
The Cove At Salem

Find out more about Gloucester

Search for holiday rentals in Gloucester on Expedia! You can easily find your home rentals, villas, holiday apartments in Gloucester using one of the methods below:

  • View our selection of featured holiday rentals in Gloucester
  • Use the map to find apartments and other holiday homes in the Gloucester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Gloucester while they last

Look no further and take a look at our great range of rental properties in Gloucester!

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?

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam: This Gloucester vacation home rental is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Another good choice for your trip to Gloucester is Peaceful centrally located home: w/ yard & walking distance to town.

How many vacation rentals are there in Gloucester?

Expedia has 158 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.