Holiday Homes in Eastern 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

Featured Holiday Homes in Eastern Massachusetts and around

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
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, (15)
"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
Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean
Interior

Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean

9.4 out of 10, Exceptional, (10)
The price is €724
includes taxes & fees
25 Aug - 26 Aug
Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable 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 €599
includes taxes & fees
8 Sept - 9 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, (51)
"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, (162)
"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
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.
House near down town Salem
Exterior

House near down town Salem

9.6 out of 10, Exceptional, (50)
"Had a weekend getaway with my mom and sister for Mothers Day and this was the perfect spot to stay! It was a quick walk across the bridge to get to downtown Salem and all of the shops and museums. Owners were super helpful and responsive, and the house was clean and beautiful. It was nice and quiet and we felt so safe the whole time. Would definitely rebook if we return to the area!! "
The price is €363
includes taxes & fees
20 Aug - 21 Aug
House near down town Salem
Entire Lower Level of the House, Across From The Beach
Beach

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (17)
"Loved getting to visit the beach and the short drive to Salem!"
The price is €325
includes taxes & fees
7 Sept - 8 Sept
Entire Lower Level of the House, Across From The Beach
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fridge, microwave, oven, stovetop

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (65)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Clean, Contemporary Escape Near T
TV, offices

Clean, Contemporary Escape Near T

8.8 out of 10, Excellent, (8)
"One parent and three teenagers in town for college tours. The location was “20” minutes via uber which was great. Everyone had room to decompress at the end of the day. Showers were great and beds were super comfortable. We will strongly consider staying there again for our next visit. "
Clean, Contemporary Escape Near T
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 Eastern Massachusetts Hotel Reviews

The Newbury Boston

The Newbury Boston

10/10 Excellent
"Awesome place to stay!"
Brian 3-night trip
Posted 1 day ago
The Newbury Boston