Holiday Homes in Massachusetts

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Top Cities in Massachusetts

Holiday HomesHoliday Homes

Boston

Boston

Featured Holiday Homes in Massachusetts

Our top choices for Massachusetts holiday homes

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

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

9.6 out of 10, Exceptional, (129)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is AU$694
includes taxes & fees
15 Sept - 16 Sept
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining

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

10.0 out of 10, Exceptional, (164)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is AU$536
includes taxes & fees
27 Aug - 28 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
Dining

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."
The price is AU$770
includes taxes & fees
1 Sept - 2 Sept
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Leslie's Retreat: Spacious home ideally located to everything
Interior

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (239)
"This property was great! Very spacious and well equipped with everything you could need."
Leslie's Retreat: Spacious home ideally located to everything
Hyannis Hideaway in Cape Cod
Paper towels

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$1,033
includes taxes & fees
7 Sept - 8 Sept
Hyannis Hideaway in Cape Cod
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (85)
"This place is so well located. So close everything. EXCELLENT.If one complaint sometimes upstairs people are very loud. Overall great stay"
The price is AU$532
includes taxes & fees
9 Sept - 10 Sept
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Beautifully Renovated Main Street Cottage- Great Location
Dining

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (117)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
2 bedrooms, free WiFi, bed sheets

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

8.4 out of 10, Very good, (24)
"The property was perfect for our family. It’s in a great location. We rented bikes and enjoyed being able to walk and bike to the beach and market. Thanks for letting us stay!"
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Sun-loungers

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

10.0 out of 10, Exceptional, (2)
"Location is very convenient to lake scargo and corporation beach! House was extremely clean. Well appointed. Had games and beach toys and chairs. Great house for family. "
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Interior

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

9.8 out of 10, Exceptional, (171)
"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
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Outdoor dining

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

9.6 out of 10, Exceptional, (42)
"We had a great weekend trip! The host was very responsive and accommodating and the property was perfect. "
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Cozy 4 bedroom cottage in town, with parking
Terrace/patio

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great stay, would stay again "
Cozy 4 bedroom cottage in town, with parking
Coastal Retreat: steps to beach and town
Exterior

Coastal Retreat: steps to beach and town

10.0 out of 10, Exceptional, (4)
"A perfect family home for a holiday in New England."
Coastal Retreat: steps to beach and town
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Outdoor dining

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (178)
"The best and the most relaxing stay in Cape Cod. Close to ocean, breathtaking views , beautiful and very comfortable house. "
The price is AU$1,376
includes taxes & fees
2 Sept - 3 Sept
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.
Sun-loungers, beach towels

Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.

9.8 out of 10, Exceptional, (116)
"The house is perfect for a large group! Excellent location & super unique, would definitely recommend!"
Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access
Smart TV, fireplace

Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

9.8 out of 10, Exceptional, (7)
"Responsive owner, noce clean quiet property. "
The price is AU$451
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (161)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Outdoor dining

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

9.8 out of 10, Exceptional, (77)
"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
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
1 bedroom, iron/ironing board, Internet, bed sheets

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.0 out of 10, Very good, (39)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
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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Top Massachusetts Hotel Reviews

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"Close to Newbury St where you can do some shopping"
palmerin 1-night trip
Posted 8 hours ago
Copley Square Hotel, a FOUND Hotel