Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
9.6 out of 10, Exceptional, (66)
"Property and location was perfect .Only minor complaint would be the noisy neighbors above. Walking/stomping back and forth all day and most of the night. It wouldn't at all keep me from staying here again. Highly recommend. "
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
Historic 1686 Home Near Downtown l 5BR Retreat
2.0 star property
10.0 out of 10, Exceptional, (5)
"My family stayed in this house for the week of October 22- the 25th. The house was just as it was pictured. The location was great as it was close to Salem. We did not have any problem checking in or out. It was very smooth. The guidebook Rachel said to download was very helpful. The house was full of antique furniture and was dated to the time period that it was built in. It was great to be able to stay in a house that was built back in the 1600's. We would stay here again and would recommend...
The price is NZ$1,165
includes taxes & fees
25 Nov - 26 Nov
Historic 1686 Home Near Downtown l 5BR Retreat
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
9.6 out of 10, Exceptional, (106)
"The property is comfortable and clean. The location is perfect, right at the harbor with an excellent cafe right across the street. I have stayed at a few VRBO properties and never had plenty of toilet paper, soap, shampoo, conditioner, trash bags, etc provided. That was a fantastic surprise. If a may make one tiny suggestion, a row of coat hooks next to the front door would be a cheap, but much appreciated addition. Again, this property is wonderful and if I make my way back to Salem I will...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Newly renovated home, top of the line appliances.
9.8 out of 10, Exceptional, (109)
"The house was beautiful, clean, spacious with everything we needed. Loved it."
Newly renovated home, top of the line appliances.
Stunning Views from Beachfront House in Manchester-by-the-Sea!
10.0 out of 10, Exceptional, (62)
"Bob was accommodating and helpful. Property was beautiful, we loved our stay. Thank you for the hospitality Bob… looking forward to a future stay!"
Stunning Views from Beachfront House in Manchester-by-the-Sea!
Beach House, Walking distance to downtown!
10.0 out of 10, Exceptional, (51)
"Lovely, clean, comfortable. Great beach access. Both Larissa and Steve were responsive and helpful. Would not hesitate to return. "
Beach House, Walking distance to downtown!
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
9.8 out of 10, Exceptional, (9)
"We had so much fun!! This house was so so great the patio was the perfect place to relax and enjoy the sea air after a long day. Our trip was for Salem but I definitely want to go back this summer just for the house! This was such a seamless and lovely stay "
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
Gloucester Home w/ Large Yard: 1 Mi to Beach!
10.0 out of 10, Exceptional, (13)
"Loved the location! The house was comfortable and quaint. The backyard and scenery were beautiful! Would definitely recommend and would stay here again!"
Gloucester Home w/ Large Yard: 1 Mi to Beach!
Leslie's Retreat: Spacious home ideally located to everything
10.0 out of 10, Exceptional, (218)
"This house was perfect for us. Plenty of room, comfortable beds, quiet neighborhood, and an easy walk to downtown. The host was very responsive and friendly. I would highly recommend starting at this property. "
Leslie's Retreat: Spacious home ideally located to everything
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
10.0 out of 10, Exceptional, (28)
"Very cute, comfortable cottage on the bay. Charming and clean amenities and furnishings. Beds were very comfortable. A bit far out from our site seeing. But routes easy enough to navigate. Off road parking was tight, and property was on Main St, so there was lots of traffic, but nothing to defer us from enjoying our stay. Definitely would recommend and stay again given the chance. This duplex cottage was more than satisfactory in every catogory. Everything you could need was there. Love...
The price is NZ$720
includes taxes & fees
25 Nov - 26 Nov
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Old Salem charm house near downtown and ocean. Great for Halloween!!
9.0 out of 10, Wonderful, (7)
"Likes: Property is close to Salem historic sites. Neighborhood is safe, close to the uni and the locals are nice. Needs work: The door to the unit cannot be locked, neighbor downstairs is loud, the kitchen needs better cleaning. "
Old Salem charm house near downtown and ocean. Great for Halloween!!
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
10.0 out of 10, Exceptional, (67)
"Property was great. Clean with plenty of space for 8 of us. Loved all the games!"
The price is NZ$1,107
includes taxes & fees
28 Nov - 29 Nov
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Plum Island place 5 minute walk to beach 9 minute walk to point
10.0 out of 10, Exceptional, (29)
"Anne was one of the best hosts I've stayed with at a VRBO property. She thought of every last detail and was extremely attentive and had a bottle of wine and chocolate treats for us when we arrived, along with a stocked kitchen of everything you need. And if you forgot something she had that too! It was very clean too. It was so close to the beach and the wildlife refuge - Plum island is such a special spot. We will be back again. We stayed for 3 nights with my elderly parents who had a...
Plum Island place 5 minute walk to beach 9 minute walk to point
Artistic Historical home, walkDT
10.0 out of 10, Exceptional, (14)
"I LOVED the convenience of this property. We walked to Essex Street and all over the downtown area of Salem. We only took our car out one time. This residence was comfortable and stocked with amenities. We loved our stay!!!"
Artistic Historical home, walkDT
Too many guests for Thanksgiving? Consider our cozy spacious family home!
10.0 out of 10, Exceptional, (24)
"This property was gorgeous and much more spacious then the photos made it appear. It was a very comfortable set up to hang out as a group as well as having some space to spread out individually. Great property for a group. Very close to Hammond Castle as well as the train station for a Boston/Salem trip with the group if you didn't want to drive. Only downside, the driveway can be a little tricky to manage at times with it being such a sharp angle off the main road and being kinda steep. If you...
Too many guests for Thanksgiving? Consider our cozy spacious family home!
Pet-Friendly Revere Getaway, Steps from the T!
10.0 out of 10, Exceptional, (37)
"Beautiful home with a short walk to the beach. This home is warm and welcoming. All the amenties you need. The owners are very responsive and have made the check-in process seemless. Revere Beach is beautiful and gives you easy access to everything Boston and beyond. We will definitely stay here again on our next visit! "
Pet-Friendly Revere Getaway, Steps from the T!
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
10.0 out of 10, Exceptional, (3)
"This place was so peaceful and relaxing "
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.
9.8 out of 10, Exceptional, (14)
"The house is simply gorgeous, the kitchen is even nicer in person! The spacious living areas accommodated our group wonderfully. The location is great, on a nice quiet street and still so close to the water!"
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.
Niles Beach House - Beach & Boston Skyline Views
8.0 out of 10, Very good, (1)
"Unlike most Vrbo locations where you work with a real person and a real home where little things like coffee filters or cooking oil, etc might be left behind for the next guest, this place was wiped clean. Also an early check in request was $80 whereas most properties work with you if they can swing it without an extra charge. There was lots of communication about the check in process which worked well, but all from the property group. Not the personal touch most properties provide. Beautiful...
Niles Beach House - Beach & Boston Skyline Views
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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Other property types in Gloucester

Good Harbor Beach House - walk to beach, close to restaurants and shopping!
10.0 out of 10, Exceptional, (192)
"The house was very warm and welcoming. It was in a great location for my son's wedding at Hammond Castle. It was fully stocked with everything you needed. We loved the deck overlooking the marsh. "
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Luxury 1900's romantic retreat steps from the beach - King Suite!
9.6 out of 10, Exceptional, (29)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
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.
Beautiful view of the beach with palm trees

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