Gloucester Holiday Rentals

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Check prices for these dates

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Holiday Rentals in Gloucester

Full-sized fridge, microwave, oven, stovetop
Long Beach Suites
Long Beach Suites
2.0 star property
9.2 out of 10, Wonderful, (52)
"Best location and it's a very nice place. "
Kylie
The price is HK$1,252
HK$2,917 total
includes taxes & fees
2 Nov - 3 Nov
Long Beach Suites
Beach nearby
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
9.8 out of 10, Exceptional, (39)
"The beach is amazing, and you can walk for hours along the shore, with the calm waters cooling your feet. Sadly, there were a lot of jellyfish, which I had never seen before in this area like this - very usual. I think it was a result of recent storms. But still, they were easy to spot and avoid. The house is comfortable and lovely and we had a great time playing games, napping and reading, and visiting. The sun porch is lovely. "
Susan F.
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
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
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. "
Charlie L.
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
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
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 "
Jess K.
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
Fridge, microwave, oven, stovetop
Peaceful centrally located home: w/ yard & walking distance to town
Peaceful centrally located home: w/ yard & walking distance to town
2.0 star property
8.4 out of 10, Very good, (10)
"Everything was perfect thank you so much for having us "
Ryan
Peaceful centrally located home: w/ yard & walking distance to town
Interior
Luxury 1900's romantic retreat steps from the beach - King Suite!
Luxury 1900's romantic retreat steps from the beach - King Suite!
9.8 out of 10, Exceptional, (47)
"Very nice spot - very clean - nice bathroom"
Mary M.
The price is HK$917
HK$2,413 total
includes taxes & fees
23 Oct - 24 Oct
Luxury 1900's romantic retreat steps from the beach - King Suite!
Private kitchen
Apartments in Salem
Apartments in Salem
3.0 star property
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. "
Wes
Apartments in Salem
Exterior
House near down town Salem
House near down town Salem
9.6 out of 10, Exceptional, (56)
"The property was an easy walk to downtown Salem. The host were east to contact and the house was a great setup for a family visiting. "
Danielle
The price is HK$1,942
HK$3,462 total
includes taxes & fees
9 Nov - 10 Nov
House near down town Salem
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!
9.8 out of 10, Exceptional, (59)
"We stayed for 3 nights and lived the decor, spells u can do and walking distant to Salem where everything is . 5 Stars ."
Regina C.
The price is HK$3,465
HK$7,460 total
includes taxes & fees
12 Nov - 13 Nov
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
Smart TV, stereo
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!
9.8 out of 10, Exceptional, (24)
"Great location. Easy access. Had a wonde Time"
Elaina D.
The price is HK$1,158
HK$2,579 total
includes taxes & fees
23 Oct - 24 Oct
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!
Interior
Leslie's Retreat: Spacious home ideally located to everything
Leslie's Retreat: Spacious home ideally located to everything
10.0 out of 10, Exceptional, (245)
"The house is stocked with just about everything that is in normal home! Very clean. There's a park just down the block on the water. We walked everywhere! The owner is awesome, we had questions and she replied quickly. "
Lisa
Leslie's Retreat: Spacious home ideally located to everything
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!
9.6 out of 10, Exceptional, (28)
"It was a very nice space. We enjoyed our time there. The views were great, the walk to the beach was nice. "
Elizabeth B.
Ocean views from every window. 5min walk to the quiet end of the beach!
TV, fireplace
Coastal Charm: Lobster Châto
Coastal Charm: Lobster Châto
2.0 star property
8.6 out of 10, Excellent, (4)
"Beautiful house & views,"
Suzanne P.
The price is HK$2,521
HK$5,933 total
includes taxes & fees
15 Nov - 16 Nov
Coastal Charm: Lobster Châto
Exterior
Quiet neighborhood and Walking destination to Downtown Salem
Quiet neighborhood and Walking destination to Downtown Salem
9.4 out of 10, Exceptional, (20)
"The area was beautiful and could walk to main Salem restaurants and shops . House was beautiful, clean and has all needed to just stay in and watch a movie and relax!!! Wou oh d stay here again!❤️"
Edna
Quiet neighborhood and Walking destination to Downtown Salem
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
9.6 out of 10, Exceptional, (141)
"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 "
HEATHER
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Smart TV
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
9.6 out of 10, Exceptional, (143)
"Property was great location, the furniture and decor definitely needs updating, very cheap and uncomfortable; especially for price of stay. "
Shaun
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Pool
Pool & Jacuzzi Escape near Boston, Salem & Marketstreet Lynnfield
Pool & Jacuzzi Escape near Boston, Salem & Marketstreet Lynnfield
The price is HK$3,107
HK$5,458 total
includes taxes & fees
21 Oct - 22 Oct
Pool & Jacuzzi Escape near Boston, Salem & Marketstreet Lynnfield
2 bedrooms, desk, iron/ironing board, travel cot
*1710 Halloween Escape/2Br House /Downtown+Parking
*1710 Halloween Escape/2Br House /Downtown+Parking
10.0 out of 10, Exceptional, (55)
"The location of this property in Salem is fantastic, everything and anything is in walking distance."
Ronald
The price is HK$2,518
HK$4,460 total
includes taxes & fees
5 Nov - 6 Nov
*1710 Halloween Escape/2Br House /Downtown+Parking
Beach nearby, sun-loungers, beach towels
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
9.8 out of 10, Exceptional, (198)
"Beautiful little getaway location! The host was great, the place was cute with all the necessities. Beautiful views!!"
Tiffany H.
The price is HK$1,515
HK$1,936 total
includes taxes & fees
19 Oct - 20 Oct
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Exterior
Whole House Steps from Pleasant Pond
Whole House Steps from Pleasant Pond
9.6 out of 10, Exceptional, (48)
"This is a clean, modern, perfect little house just a stone’s throw from a clean, quiet perfect little swimming pond. Communication with host easy, check in easy, The neighbors are very friendly, we hope to return next summer. "
Lara G.
Whole House Steps from Pleasant Pond
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 Vista

The Vista

10/10 Excellent
"Lovely quant property. A little dated but the upkeep is well done. Breakfast was good however seating is mainly outside no matter the weather. "
Cheryl 2-night trip
Posted 11 hours ago
The Vista

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
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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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a fireplace, a selection of games and a BBQ 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 that you can cook with friends or family. Some other top choices in Gloucester are Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24 and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many holiday rentals are there in Gloucester?

Expedia has 156 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 Pavilion Beach and Half Moon Beach 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 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.