Holiday Homes in Eastern Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Eastern Massachusetts and around

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

9.8 out of 10, Exceptional, (168)
"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

10.0 out of 10, Exceptional, (238)
"We rented this house to stay for my son’s wedding in Salem. The house was fantastic and quaint. Megan is a great host and very responsive. Would definitely rent again if we’re in Salem!"
Leslie's Retreat: Spacious home ideally located to everything

"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 €787
includes taxes & fees
20 Aug - 21 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

10.0 out of 10, Exceptional, (160)
"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

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 €613
includes taxes & fees
8 Sept - 9 Sept
Hyannis Hideaway in Cape Cod

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

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

9.8 out of 10, Exceptional, (6)
"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

9.8 out of 10, Exceptional, (48)
"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
8 Sept - 9 Sept
Ocean Breeze Motel - Standard Double

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 €329
includes taxes & fees
14 Aug - 15 Aug
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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!

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

9.8 out of 10, Exceptional, (75)
"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.

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.

Cloud 9 Lounge - Aviation-Themed Designer Flat

Cloud 9 Lounge - Aviation-Themed Designer Flat

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 €383
includes taxes & fees
18 Aug - 19 Aug
House near down town Salem

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 €350
includes taxes & fees
10 Sept - 11 Sept
Entire Lower Level of the House, Across From The Beach

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
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Eastern Massachusetts Hotel Reviews