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Our top choices for Gloucester holiday homes

1. 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 £298
includes taxes & fees
10 Nov - 11 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking

2. 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, (24 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 £476
includes taxes & fees
11 Nov - 12 Nov
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (18 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 £154
includes taxes & fees
9 Nov - 10 Nov
The Essex of Gloucester

4. 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 £649
includes taxes & fees
9 Nov - 10 Nov
Classic Coastal Family Home | Walk to Sea;King Bed

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 £590
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 £331
includes taxes & fees
9 Nov - 10 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 £578
includes taxes & fees
11 Nov - 12 Nov
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

8. 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.
Experience Classic New England-walk to beach&shops

9. Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping
Rockport
9.8 out of 10, Exceptional, (10 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 £490
includes taxes & fees
9 Nov - 10 Nov
Historic Renovation, Walk to Front Beach and Shopping

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 £427
includes taxes & fees
17 Nov - 18 Nov
Brackett Cottage: Near Salem! Heart of Historic Marblehead; Walk to Shops & Dining

11. 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)
"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...
United States
Maura
The price is £260
includes taxes & fees
9 Nov - 10 Nov
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

12. 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 £295
includes taxes & fees
9 Nov - 10 Nov
Plovers Nest

13. 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)
"We enjoyed our stay at this property. It is in a great location. Easy to walk to restaurants and stores in Marblehead. It was nice to not have to spend more time in our car after driving from Georgia. Property had everything we needed to live comfortably during our stay."
United States
Kevin H.
The price is £353
includes taxes & fees
7 Dec - 8 Dec
Historic Marblehead Nautical Home • Minutes to Salem

14. 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 £437
includes taxes & fees
9 Dec - 10 Dec
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

15. 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 £650
includes taxes & fees
9 Nov - 10 Nov
Rockmere Inn: Colonial Charm – Celebrate 250 Years in Historic Marblehead!

16. 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 £319
includes taxes & fees
9 Nov - 10 Nov
Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

17. 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 £375
includes taxes & fees
11 Nov - 12 Nov
Ospreys Landing: a Charming Plum Island Cottage close to Historic Newburyport

18. Heights House - 93 Walkscore~Halloween~Grill

Heights House - 93 Walkscore~Halloween~Grill
Salem
9.2 out of 10, Wonderful, (5 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 £266
includes taxes & fees
18 Nov - 19 Nov
Heights House - 93 Walkscore~Halloween~Grill

19. Beverly 5BR • 1686 Historic • Beach • Firepit • Sleeps 8

Beverly 5BR • 1686 Historic • Beach • Firepit • Sleeps 8
Beverly
9.6 out of 10, Exceptional, (18 reviews)
"What a beautiful, historic property!!! Ideal for families or large groups visiting the area. Plenty of parking space! Don’t think twice about booking. Communication with the host was perfection. 5 stars for sure!"
United States
Kristen L.
The price is £539
includes taxes & fees
9 Nov - 10 Nov
Beverly 5BR • 1686 Historic • Beach • Firepit • Sleeps 8

20. The Nest | High-End Kitchen | Steps to Beach | A/C

The Nest | High-End Kitchen | Steps to Beach | A/C
Newbury
10.0 out of 10, Exceptional, (15 reviews)
"Perfect spot for beach, restaurants and Newbury port See you next summer!"
United States
Sebastien L.
The price is £352
includes taxes & fees
9 Nov - 10 Nov
The Nest | High-End Kitchen | Steps to Beach | A/C
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.