Holiday Homes in Gloucester

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Our top choices for Gloucester holiday homes

1. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (19 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.
The price is NZ$448
includes taxes & fees
7 Dec - 8 Dec
The Essex of Gloucester

2. 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, (9 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.
The price is NZ$1,546
includes taxes & fees
18 Nov - 19 Nov
Classic Coastal Family Home | Walk to Sea;King Bed

3. 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
9.6 out of 10, Exceptional, (25 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
The price is NZ$1,009
includes taxes & fees
16 Nov - 17 Nov
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (16 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.
The price is NZ$846
includes taxes & fees
29 Nov - 30 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking

5. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
East Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"We truly enjoyed our time at the Mariner. Its a beautiful home with all the necessary amenities. Rachel is an excellent host. She was extremely responsive throughout our stay. We will definitely be back!!"
United States
Nina R.
The price is NZ$1,390
includes taxes & fees
24 Nov - 25 Nov
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

6. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (45 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is NZ$823
includes taxes & fees
16 Nov - 17 Nov
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

7. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (38 reviews)
"Great spot right on Long Beach! Has great views of the ocean right on the water. We definitely stay there again pet friendly."
United States
Emmy D.
The price is NZ$1,172
includes taxes & fees
15 Nov - 16 Nov
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

8. Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping
Rockport
10.0 out of 10, Exceptional, (11 reviews)
"This house worked well for our family with seven people of all ages and really enjoyed our first trip to the Rockport/Gloucester area. Hopefully we'll get a chance to return and would highly recommend the area and property."
United States
Dan K.
The price is NZ$1,125
includes taxes & fees
13 Nov - 14 Nov
Historic Renovation, Walk to Front Beach and Shopping

9. Experience Classic New England-walk to beach&shops

Experience Classic New England-walk to beach&shops
Rockport
10.0 out of 10, Exceptional, (2 reviews)
"What a delightful and welcoming space to enjoy with our family. We even had a dedicated puzzle room. Everything you need is there. The beds are very comfortable and the rooms are quiet places to rest. You can’t go wrong renting this home."
United States
J P.
The price is NZ$1,586
includes taxes & fees
2 Dec - 3 Dec
Experience Classic New England-walk to beach&shops

10. Brackett Cottage: Near Salem! Heart of Historic Marblehead; Walk to Shops & Dining

Brackett Cottage: Near Salem! Heart of Historic Marblehead; Walk to Shops & Dining
Marblehead Historic District
The price is NZ$1,136
includes taxes & fees
15 Nov - 16 Nov
Brackett Cottage: Near Salem! Heart of Historic Marblehead; Walk to Shops & Dining

11. 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, (34 reviews)
"Great place - very convenient and comfortable! Great host!"
United States
Jeanni S.
The price is NZ$2,259
includes taxes & fees
1 Dec - 2 Dec
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

12. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.8 out of 10, Exceptional, (8 reviews)
"The small cottage was clean and well kept. The location was perfect-a short walk to the beach but isolated from the noise of Salisbury Center. Also a short walk from Seaglass, our favorite restaurant and lounge. And when we decided to extend our stay by a day, the host was very communicative, helpful and agreeable. We will be back!"
United States
Scott R.
The price is NZ$632
includes taxes & fees
13 Nov - 14 Nov
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

13. Plovers Nest

Plovers Nest
3.0 star property
Newburyport
10.0 out of 10, Exceptional, (2 reviews)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
The price is NZ$680
includes taxes & fees
17 Nov - 18 Nov
Plovers Nest

14. Historic Marblehead Nautical Home • Minutes to Salem

Historic Marblehead Nautical Home • Minutes to Salem
Marblehead Historic District
10.0 out of 10, Exceptional, (27 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is NZ$828
includes taxes & fees
7 Dec - 8 Dec
Historic Marblehead Nautical Home • Minutes to Salem

15. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing
Salisbury Beach
10.0 out of 10, Exceptional, (1 review)
The price is NZ$780
includes taxes & fees
13 Nov - 14 Nov
Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

16. Rockmere Inn: Colonial Charm – Celebrate 250 Years in Historic Marblehead!

Rockmere Inn: Colonial Charm – Celebrate 250 Years in Historic Marblehead!
Marblehead Historic District
The price is NZ$1,575
includes taxes & fees
17 Nov - 18 Nov
Rockmere Inn: Colonial Charm – Celebrate 250 Years in Historic Marblehead!

17. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Marblehead
9.8 out of 10, Exceptional, (29 reviews)
"We stayed in the property for one night, so we were in and out. The house is older, but everything works great and it was super clean. The beds were very comfortable. The view from the back year/deck is simply amazing. The ocean, the lighthouse, the boats are just beautiful and is worth every bit of what we paid. I didn’t have a need to communicate with the host but all check in and check out directions were sufficient."
United States
Hayley H.
The price is NZ$998
includes taxes & fees
9 Dec - 10 Dec
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

18. Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
Newburyport
9.8 out of 10, Exceptional, (93 reviews)
"Cute little place that is clean and well taken care of. Plum Island was adorable with a mile walk or ride to a great beach. Enjoyed our stay."
United States
Ann P.
The price is NZ$683
includes taxes & fees
17 Nov - 18 Nov
Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

19. Heights House - 93 Walkscore~Halloween~Grill

Heights House - 93 Walkscore~Halloween~Grill
Salem
9.4 out of 10, Exceptional, (6 reviews)
"Apartment was very clean and close to downtown Salem but on a quiet block. Host was very responsive and helpful. Would definitely stay here again. "
United States
Steve R.
The price is NZ$606
includes taxes & fees
18 Nov - 19 Nov
Heights House - 93 Walkscore~Halloween~Grill

20. Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport
Newburyport
8.0 out of 10, Very good, (2 reviews)
"Cute little cottage. Incredible location near one of the most beautiful towns and long pristine beaches and natural habitat preserves I've encountered. We used to go to Plum Island when I was a kid and when my kids were young. Even more interesting than I remembered.The house has a nice, well-furnished kitchen, and it's a lovely, small, cozy space. The only issues we had were furniture, inside seating, and a very loud washer and dryer. It's a tiny place that maximizes space so well it kind of...
United States
Tim S.
The price is NZ$824
includes taxes & fees
16 Nov - 17 Nov
Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport
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.

Learn more about Gloucester

America's oldest working seaport offers whale watching tours where humpback sightings are common from May through October. Wander the colourful harborfront where fishermen unload their catch, then sample the freshest lobster rolls at family-owned seafood shacks along Rocky Neck.

A harbor with boats, including a 'Whale Watch' and a 'Wejack' named boat.

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