Holiday Homes in Eastern Massachusetts

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Featured Holiday Homes in Eastern Massachusetts

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

10.0 out of 10, Exceptional, (14)
"We had a great time at Captains lookout. The pictures were accurate and we love the view from the roof. The host was very accommodating and helpful. "
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

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

9.6 out of 10, Exceptional, (126)
"We stayed here for four days. It’s very clean nice beautiful place."
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

9.4 out of 10, Exceptional, (8)
The price is AU$1,393
includes taxes & fees
12 Aug - 13 Aug
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (160)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is AU$583
includes taxes & fees
14 Aug - 15 Aug
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

10.0 out of 10, Exceptional, (94)
"Loved our stay. Property is very clean and in a quiet neighborhood close to town and beaches. Host Bonnie was great. Would definitely rent again."
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

9.8 out of 10, Exceptional, (167)
"So much better than staying at a hotel and separating our group of seven. Awesome stay, 10 out of 10 recommend"
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Centrally located charmer with expansive patio, board games, & central AC

7.6 out of 10, Good, (9)
"Beautiful property"
Centrally located charmer with expansive patio, board games, & central AC

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is AU$1,226
includes taxes & fees
3 Sept - 4 Sept
Hyannis Hideaway in Cape Cod

Union Square House

9.6 out of 10, Exceptional, (77)
"Had a wonderful stay. Location great. House as described, clean, and comfortable. Would recommend for a stay. "
Union Square House

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (237)
"We loved staying here! If we ever come back to Salem this is our first choice!"
Leslie's Retreat: Spacious home ideally located to everything

Charming house with WiFi and AC in superb Randolph

9.6 out of 10, Exceptional, (9)
"This was a lovely little home in a quiet neighborhood that allowed us easy access to the highway for our daily adventures. The host was fabulous! We would definitely choose to stay there again if we ever return to the Boston area."
Charming house with WiFi and AC in superb Randolph

Spacious, New Renovation | Near T

10.0 out of 10, Exceptional, (7)
"The house was very nice, clean and comfortable. Had all the supplies we needed plus more included. Check-in and check-out were both super smooth. The host was very responsive. Overall great stay!"
Spacious, New Renovation | Near T

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (56)
"Great location easy to get to all of Boston, clean and well maintained, large kitchen and living room. Enjoyed our stay"
Boston's Best Vacation Home

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

9.6 out of 10, Exceptional, (83)
"This property is perfect for 2 travelers or for a small family. Close to everything, very clean and easy to get to. Would 100% stay here again!"
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Charming Newly Renovated 4 Bedroom Home walking distance to Egypt Beach

10.0 out of 10, Exceptional, (2)
"Great communication! Great location for us. The house was in such great shape! We would totally rent again! Wonderful stay "
Charming Newly Renovated 4 Bedroom Home walking distance to Egypt Beach

Whole House Steps from Pleasant Pond

9.6 out of 10, Exceptional, (43)
"Beautiful area next to the pond, quiet and peaceful!"
Whole House Steps from Pleasant Pond

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (21)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
The price is AU$645
includes taxes & fees
23 Aug - 24 Aug
Hidden Gem right in the city of Boston!

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (16)
"Loved getting to visit the beach and the short drive to Salem!"
The price is AU$609
includes taxes & fees
6 Aug - 7 Aug
Entire Lower Level of the House, Across From The Beach

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (74)
"Had the best family vacation at the Rocky Neck Hideaway, from the location, to the host, to the amenities, everything was excellent. The whole stay exceeded our expections and we will be back! "
"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.
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