Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

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

9.6 out of 10, Exceptional, (110)
"Our third stay at 14 Hodges. We were so pleased with the upgrades. The new beds/bedding were amazing and the new thermostat was user friendly. We managed to cook quite a bit while also eating out at our favorite vegan spots in Salem and Beverly. We headed to Boston via train for the Titanic exhibit and headed to Portland Maine and the lit up for the Holidays Nubble Light House. It was great to visit the PEM once again for some great exhibits and all the local stores. It was great to be "home." "
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (24)
"What a wonderful home! The beds were incredibly comfortable and the linens high-quality. The house was very clean and simply furnished, and everything felt very nice and substantial. It was a lovely place and a lovely rental process. We would definitely come back."
Beach Life Bliss - steps to the beach

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

9.6 out of 10, Exceptional, (9)
"Loved this old historic home and the town. Had everything we needed to make our stay comfortable. Would love to come back again! Everything was walkable. Charming town. Gorgeous ocean all around. In love!"
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (71)
"It’s hard to imagine a more convenient location in central Salem. This historic building is across the street from the Peabody Essex Museum and close to restaurants and bars, but it’s relatively quiet in November. (The only sounds at night were some footsteps from the apartment above.) The interior was clean and appointed with everything we needed for our stay. I especially appreciated the coffee maker and coffee pods and the washing machine in the unit. All in all a very comfortable stay and...
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

10.0 out of 10, Exceptional, (51)
"Everything you could ask for"
The price is NZ$811
includes taxes & fees
23 Jan - 24 Jan
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Wonderful home sitting right between two terrific beaches!

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...
Wonderful home sitting right between two terrific beaches!

"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

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

Charming private townhouse-style lodging, a block from Marblehead Harbor

10.0 out of 10, Exceptional, (124)
"Outstanding in all respects. Wonderful host and superb property. We'll definitely be back!"
Charming private townhouse-style lodging, a block from Marblehead Harbor

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

9.8 out of 10, Exceptional, (31)
"We visited Gloucester with our 3 adult children and the 5 of us had plenty of space in this great home. Walking distance to great lobster, coffee shops and bakeries. "
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

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

10.0 out of 10, Exceptional, (70)
"We had a big group stay for NYE, had the best time staying in at this house, plenty to do inside and plenty of space for everyone! "
The price is NZ$1,146
includes taxes & fees
24 Jan - 25 Jan
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location

9.8 out of 10, Exceptional, (92)
"We’ve stayed at Plum Island for years and this was our first time booking this home. It was perfect for our Thanksgiving getaway with extended family- three generations under one roof! So close to the beach and the wildlife preserve as well. Highly recommend! "
Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location

Pet-Friendly Revere Getaway, Steps from the T!

10.0 out of 10, Exceptional, (40)
"We highly recommend a stay here when in Boston! The house is very comfortable, well-kept and in a nice location. The T station is just a few blocks away, making trips into the city very easy. Revere Beach is within walking distance, and was a daily highlight of our trip. The hosts were very responsive and accommodating. We had an unexpected issue come up and needed to extend our stay. Sean promptly and graciously helped us work with Evolve to secure the extra nights needed.We look forward...
Pet-Friendly Revere Getaway, Steps from the T!

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!

NEW Tiny House Walk to Essex Main St+Boat Launch

10.0 out of 10, Exceptional, (4)
"Perfect location, quiet, clean and comfortable! Would recommend! We enjoyed being so close to our family in Ipswich and Hamilton. Thank you!!"
NEW Tiny House Walk to Essex Main St+Boat Launch

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

The price is NZ$653
includes taxes & fees
23 Jan - 24 Jan
2 Bed/2 Bath Private Beach House One Block from the ocean.

Seaside retreat: Steps to beach, board walk. 3 car parking, deck, BBQ.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family of 6 stayed here for just two nights, and we all wished we could stay longer. The bedroom set-ups fit our family group perfectly, the whole house was sparkling clean, and the kitchen appliances and cookware were all really nice. Ediola even provided coffee and some seasonal welcome cookies. She also made a special delivery of more coffee to suit our preferences the following day as well as hot cocoa mix. The location is perfect, and the end of a small lane, truly just a 3 minute...
Seaside retreat: Steps to beach, board walk. 3 car parking, deck, BBQ.

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"Easy walk to the beach and town. Great family space. "
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (1)
"My family & I booked a trip to Salem and we desired to find a cute home that would accommodate 7 of us that was within walking distance of downtown Salem and we found just that in this home! The host was a great communicator & really was fantastic at making our stay welcoming and pleasant. We were able to walk to all the tourist sites and restaurants within a short amount of time. Would recommend staying here 10/10. "
The price is NZ$879
includes taxes & fees
18 Feb - 19 Feb
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
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

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (24)
"What a wonderful home! The beds were incredibly comfortable and the linens high-quality. The house was very clean and simply furnished, and everything felt very nice and substantial. It was a lovely place and a lovely rental process. We would definitely come back."
Beach Life Bliss - steps to the beach

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

9.6 out of 10, Exceptional, (32)
"This property was perfect! It was clean, comfortable and cozy. It was 2 miles from our family and we enjoyed being close to the water and town as well. The bed was comfortable, which isn't often the case in a rental. We didn't want to leave!"
Luxury 1900's romantic retreat steps from the beach - King Suite!

"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
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.