Holiday Homes in Massachusetts

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Top Cities in Massachusetts

Holiday HomesHoliday Homes

Boston

Boston

Featured Holiday Homes in Massachusetts

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
Fridge, microwave, oven, stovetop

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

8.2 out of 10, Very good, (37)
"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
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, (169)
"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
3 Mi to Beach: Historic Farmhouse on Cape Cod!
Fridge, microwave, stovetop, dishwasher

3 Mi to Beach: Historic Farmhouse on Cape Cod!

9.6 out of 10, Exceptional, (4)
"Wonderful Stay. Home was very clean, well stocked and convienient to shops and restaurants. Beds were comfortable and the home fit our family well."
3 Mi to Beach: Historic Farmhouse on Cape Cod!
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)
"If you are ever in need of a decent sized house for extended family during graduation (ours was at Endicott) this is the place! Convenient, Clean and so many beds to accommodate everyone comfortably (including our dog). It was great… thank you!"
Leslie's Retreat: Spacious home ideally located to everything
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
Fridge, microwave, oven, stovetop

"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
Interior

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

9.6 out of 10, Exceptional, (127)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is €391
includes taxes & fees
15 Sept - 16 Sept
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Fridge, microwave, oven, stovetop

Quaint getaway with full kitchen and lush yard - close to the beach and downtown

9.2 out of 10, Wonderful, (121)
"We liked the location. It was close enough to walk to town. House had everything we needed and the 2 coffee pots was a plus for us."
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
Interior

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

9.4 out of 10, Exceptional, (10)
The price is €727
includes taxes & fees
24 Aug - 25 Aug
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
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
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 €608
includes taxes & fees
16 Sept - 17 Sept
Hyannis Hideaway in Cape Cod
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

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

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi
Exterior

Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

9.6 out of 10, Exceptional, (8)
"We had a phenomenal stay at this property. It was a group of friends coming together to watch a play at the Cape Playhouse. The house was pristine, beautifully decorated and everyone slept great on the beds and linens. Highly recommend!"
Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi
Ocean Breeze Motel - Standard Double
Beach

Ocean Breeze Motel - Standard Double

9.8 out of 10, Exceptional, (50)
"Clean, comfortable hotel with good sized room and great shower. Good coffee and breakfast included with many options. Joanna, the owner was very helpful with suggestions in the area- biking, beach, sunsets, sea food restaurants. Had a great stay! "
The price is €180
includes taxes & fees
7 Sept - 8 Sept
Ocean Breeze Motel - Standard Double
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, (161)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is €301
includes taxes & fees
27 Aug - 28 Aug
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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!

8.2 out of 10, Very good, (23)
"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!
"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, (76)
"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
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!
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.
Charming coastal home near pond with sunroom, open layout, yard & AC
Fridge, microwave, oven, stovetop

Charming coastal home near pond with sunroom, open layout, yard & AC

9.4 out of 10, Exceptional, (3)
"Great location and house. Enjoyed it very much! "
Charming coastal home near pond with sunroom, open layout, yard & AC
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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Very friendly staff. Comfortable and clean"
Jane 2-night trip
Posted 3 hours ago
Seaport Hotel Boston