Gloucester Vacation Rentals

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Check prices for these dates

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Dec 30 - Dec 31
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Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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
Beach
Long Beach Suites: 3 Mins Toes To Sand!

Apartment in East Gloucester

Long Beach Suites: 3 Mins Toes To Sand!
8.8 out of 10, Excellent, (19)
"After a conference in Boston, we wanted go stay a few days in a relaxed area near the sea. It was lovely and quiet, and a short walk to the beach."
United States
Jennifer T.
The price is ￥18,248
￥60,584 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Long Beach Suites: 3 Mins Toes To Sand!
Private kitchen
The Essex of Gloucester

Vacation Home in Gloucester

The Essex of Gloucester
2.0 star property
The price is ￥22,460
￥28,572 total
includes taxes & fees
Jan 1 - Jan 2, 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 ￥19,013
￥59,738 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Dining
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Vacation Home in Gloucester

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
10.0 out of 10, Exceptional, (7)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is ￥35,226
￥86,734 total
includes taxes & fees
Jan 4 - Jan 5, 2026
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
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, (36)
"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 ￥17,539
￥57,920 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
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
1BR with Private Deck + Ocean Views· Private Parking · King Bed
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.
The price is ￥16,377
￥40,942 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Harborside Oasis ★ Harbor View ★ Heart of Downtown
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, (30)
"Great place for the two of us, centrally located and met all of our expectations."
United States
Charles S.
The price is ￥13,920
￥37,676 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
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 ￥11,738
￥25,175 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Dusk Suite at The Hygge House, Dusk Suite at The Hygge House
Marina
The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·

Apartment in Rockport

The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
10.0 out of 10, Exceptional, (31)
"Great location. Excellent and clean renovation and a very responsive host. "
United States
Ken W.
The price is ￥19,013
￥52,074 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
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 ￥18,093
￥51,432 total
includes taxes & fees
Dec 31 - Jan 1, 2026
1 Mi to Downtown: Salem Vacation Rental!
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 ￥10,169
￥34,357 total
includes taxes & fees
Dec 31 - Jan 1, 2026
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
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 ￥20,120
￥60,629 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
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 ￥14,817
￥33,540 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Comfy King Beds~5 min to Salem
Fridge, microwave, oven, stovetop
Re-listed: Adorable Condo Beverly - Salem - Halloween

Apartment in Beverly

Re-listed: Adorable Condo Beverly - Salem - Halloween
9.8 out of 10, Exceptional, (19)
"Small, clean ,quiet , great location Work definitely rent again"
United States
Nick S.
The price is ￥14,591
￥38,598 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Re-listed: Adorable Condo Beverly - Salem - Halloween
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 ￥19,652
￥59,931 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Oceanfront Oasis | 2BR Monthly | Salisbury
Exterior detail
Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Condo in Marblehead

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
2.0 star property
10.0 out of 10, Exceptional, (2)
"This place is awesome. First time going to the east and I’d rather stay here over any 5 star hotel. Janie is so nice n gave some great suggestions for bars/places to eat while there. The only bad part about the trip was having to go home. Easy parking, fairy tale like back yard area, historic house, and only a 4 minute walk to the ocean. "
United States
Madison J.
The price is ￥11,604
￥31,777 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
On the beach
Hampton Tides | Ocean Views | Top Floor Balcony

Apartment in Hampton

Hampton Tides | Ocean Views | Top Floor Balcony
9.6 out of 10, Exceptional, (4)
"Very clean and quiet. Excellent ocean view. Overall a great experience."
United States
Donna H.
The price is ￥21,368
￥55,510 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hampton Tides | Ocean Views | Top Floor Balcony
Fridge, microwave, oven, stovetop
The Nest • Luxury Monthly Stay • Across from Beach

Vacation Home in Newbury

The Nest • Luxury Monthly Stay • Across from Beach
10.0 out of 10, Exceptional, (14)
"Very nice and comfortable stayHad everything we neededGreat location Could use some better beach chairsOnly had one good one."
United States
Joseph W.
The price is ￥25,891
￥66,605 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Nest • Luxury Monthly Stay • Across from Beach
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
"Staff was super friendly and helpful and rooms were spacious and comfortable. Good option for day or two in Salem."
Steven 2-night trip
Posted 1 day 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.