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Gloucester Holiday Rentals

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Check prices for these dates

Tonight
14 Dec - 15 Dec
Tomorrow
15 Dec - 16 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Gloucester holiday rentals

On the beach, sun-loungers, beach towels
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
Gloucester
9.4 out of 10, Exceptional, (61)
"Beautiful home, close to the beach. Air conditioning wasn’t great and fridge didn’t get very cold. Enjoyed the deck space "
United States
Jess K.
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
Beach nearby
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Gloucester
9.8 out of 10, Exceptional, (39)
"We had a great stay here - the house was very comfortable and welcoming and just steps away from the beach! The owner is very responsive and helpful. Would absolutely stay here again!"
United States
Piper T.
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Beach nearby, sun-loungers, beach towels
Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Good Harbor Beach House - walk to beach, close to restaurants and shopping!
East Gloucester
10.0 out of 10, Exceptional, (218)
"very sweet cottage, well equipped kitchen. location great, quiet neighborhood ."
United States
nancy g.
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Fridge, microwave, oven, stovetop
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
East Gloucester
10.0 out of 10, Exceptional, (3)
"It was a beautiful home. Clean, up-to-date, and conveniently located. The host was very attentive and helpful. "
United States
Charlie L.
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
Interior
Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (49)
"Very nice spot - very clean - nice bathroom"
United States
Mary M.
Luxury 1900's romantic retreat steps from the beach - King Suite!
Fridge, microwave, oven, stovetop
Peaceful centrally located home: w/ yard & walking distance to town

Peaceful centrally located home: w/ yard & walking distance to town

Peaceful centrally located home: w/ yard & walking distance to town
2.0 star property
Gloucester
8.6 out of 10, Excellent, (11)
"Everything was perfect thank you so much for having us "
United States
Ryan
Peaceful centrally located home: w/ yard & walking distance to town
Outdoor dining
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
East Gloucester
10.0 out of 10, Exceptional, (37)
"The property was exactly as advertised. The host was very helpful and responsive. The house was very clean and in a great location. The access to the beach was terrific and the proximity to both Rockport and Gloucester made both easily accessible. We enjoyed our stay."
United States
Jeffrey H.
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
A heated pool
Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach

Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach

Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach
East Gloucester
6.8 out of 10, (3)
"This was the perfect property for our family. The house is wonderful and the hosts are super responsive. We can’t wait to return!"
United States
Bridget D.
Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach
Beach
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
Downtown Salem
9.6 out of 10, Exceptional, (61)
"Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!"
United States
More M.
The price is HK$2,421
HK$5,847 total
includes taxes & fees
15 Dec - 16 Dec
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
Interior
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything
Salem
10.0 out of 10, Exceptional, (251)
"Great location, walking distance to everything! Beautiful well kept home."
United States
Susan G.
Leslie's Retreat: Spacious home ideally located to everything
Interior
Luxury and Modern Apt near Mall/ Hospital

Luxury and Modern Apt near Mall/ Hospital

Luxury and Modern Apt near Mall/ Hospital
Danvers
10.0 out of 10, Exceptional, (49)
"Amazing stay! Met our needs perfectly. Walkable restaurants and coffee shop. Highly recommend this property."
United States
Paul M. P.
The price is HK$1,946
HK$3,730 total
includes taxes & fees
15 Dec - 16 Dec
Luxury and Modern Apt near Mall/ Hospital
Private kitchen
Apartments in Salem

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
Apartments in Salem
Smart TV
1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.

1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.

1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.
2.0 star property
Salem
10.0 out of 10, Exceptional, (3)
"This house is absolutely beautiful, perfect location for all the convince of down town and the host was a sweetheart! "
United States
Shelby L.
The price is HK$1,557
HK$1,991 total
includes taxes & fees
15 Dec - 16 Dec
1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.
Exterior
Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights
Salem
9.6 out of 10, Exceptional, (58)
"it was very nice and cozy definitely go back there again "
United States
Doreen
The price is HK$1,752
HK$3,226 total
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Salem Getaway. Historic Home Near All the Sights
Interior
Ocean views from every window. 5min walk to the quiet end of the beach!

Ocean views from every window. 5min walk to the quiet end of the beach!

Ocean views from every window. 5min walk to the quiet end of the beach!
Hampton Beach
9.6 out of 10, Exceptional, (28)
"It was quick but memorable next time we will stay longer, accomodations were great, location has everything."
United States
Bonnie B.
Ocean views from every window. 5min walk to the quiet end of the beach!
Fridge, microwave, oven, stovetop
The Lighthouse - Perfect Location Near Beach

The Lighthouse - Perfect Location Near Beach

The Lighthouse - Perfect Location Near Beach
Hampton Beach
9.8 out of 10, Exceptional, (17)
"Tight squeeze but very nice for a HB stopover."
United States
Richard Brian T.
The Lighthouse - Perfect Location Near Beach
Interior
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Salem
9.6 out of 10, Exceptional, (146)
"Great place The one and only negative was the smell of POT when you opened door to unit. Otherwise, what a great place, beautiful, clean, close to everything. Would definitely stay again "
United States
HEATHER
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Exterior
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Hampton Beach
10.0 out of 10, Exceptional, (102)
"This is an amazing property to stay at! The property owner is extremely responsive to ALL texts and requests. I highly recommend staying here!"
United States
Darlene S.
The price is HK$2,335
HK$4,823 total
includes taxes & fees
15 Dec - 16 Dec
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Smart TV
2 Bed/2 Bath Private Beach House One Block from the ocean.

2 Bed/2 Bath Private Beach House One Block from the ocean.

2 Bed/2 Bath Private Beach House One Block from the ocean.
Hampton Beach
10.0 out of 10, Exceptional, (18)
"Everything was wonderful! Location is perfect, we can’t wait to come back!"
United States
Melanie L.
2 Bed/2 Bath Private Beach House One Block from the ocean.
Beach nearby
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.
Rockport
10.0 out of 10, Exceptional, (22)
"The house was a perfect home base for our extended family vacation. The house is the best equipped of any of the VRBOs I have ever stayed at. We all loved it. "
United States
Mark B.
The price is HK$3,199
HK$8,852 total
includes taxes & fees
15 Dec - 16 Dec
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.
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

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

10/10 Excellent
"Friendliness of staff was the best, both check in and out, also the duration of stay Excellent accommodation Thank you "
Neal 2-night trip
Posted 1 day ago
DoubleTree by Hilton Boston North Shore

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 holiday rental in Gloucester?

Yes, there are holiday rentals in Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Gloucester has to offer?

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam: This highly rated holiday home rental in Gloucester is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Gloucester are Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24 and Peaceful centrally located home: w/ yard & walking distance to town.

How many holiday rentals are there in Gloucester?

Expedia has 160 holiday 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. Cape Ann Museum and Rocky Neck Art Colony are other places to visit while you're in town.

What are holiday rentals like in Gloucester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gloucester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.