Holiday Homes in Massachusetts

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Massachusetts Accommodation: Most Popular Cities to Stay

Featured Holiday Homes in Massachusetts

Our top choices for Massachusetts holiday homes

Casa Castor • Private Room 1

9.0 out of 10, Wonderful, (2)
"We loved staying at Judith's place! Much recommended!"
The price is £101
includes taxes & fees
18 Sept - 19 Sept
Casa Castor • Private Room 1

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

9.6 out of 10, Exceptional, (86)
"Perfect location. "
The price is £212
includes taxes & fees
17 Sept - 18 Sept
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

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

10.0 out of 10, Exceptional, (165)
"Beautiful cottage , great location. Would love to stay again "
The price is £581
includes taxes & fees
12 Oct - 13 Oct
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (241)
"Magnificently well maintained home near everything. Great for a large family vacation. "
Leslie's Retreat: Spacious home ideally located to everything

Renovated cottage 1 mile to beach in Chatham!

9.8 out of 10, Exceptional, (75)
"Great cottage, everything we needed for a really relaxing time. Good location close to everything we needed (by car). "
Renovated cottage 1 mile to beach in Chatham!

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 £468
includes taxes & fees
15 Sept - 16 Sept
Hyannis Hideaway in Cape Cod

Cozy Pet-Friendly 4BR | Fireplace, Patio and BBQ

Cozy Pet-Friendly 4BR | Fireplace, Patio and BBQ

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

9.8 out of 10, Exceptional, (118)
"Lau was wonderful and communicated so quickly. The house is in a great location, easy walk to the beach. "
Ocean view spacious 5-bedroom Cape Cod style house with roof deck, AC, WiFi.

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

10.0 out of 10, Exceptional, (169)
"Perfect spot for a few days away with the kids. The house had everything we needed and was in a great location! Would definitely rent again. "
The price is £236
includes taxes & fees
22 Sept - 23 Sept
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

9.6 out of 10, Exceptional, (132)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is £336
includes taxes & fees
15 Sept - 16 Sept
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Hidden Gem right in the city of Boston!

9.6 out of 10, Exceptional, (22)
"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."
Hidden Gem right in the city of Boston!

House near down town Salem

9.6 out of 10, Exceptional, (52)
"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 £334
includes taxes & fees
16 Sept - 17 Sept
House near down town Salem

Tiny Home with AC and WiFi in lovely Ludlow

9.0 out of 10, Wonderful, (6)
The price is £113
includes taxes & fees
10 Oct - 11 Oct
Tiny Home with AC and WiFi in lovely Ludlow

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.2 out of 10, Wonderful, (19)
"Great stay, would stay again "
Cozy 4 bedroom cottage in town, with parking

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

10.0 out of 10, Exceptional, (3)
"We had such an amazing stay! The house was absolutely beautiful and had so much space for our family to relax and enjoy. The pool was incredible — the kids practically lived in it the whole trip! The hot tub was also a wonderful bonus! Everything was clean, comfortable, and even better than expected. The hosts were fantastic — quick to answer any questions and made sure we had everything we needed. We would definitely stay here again and highly recommend it to anyone looking for a perfect...
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

Love Sand, Madaket on the Beach, Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is £794
includes taxes & fees
15 Sept - 16 Sept
Love Sand, Madaket on the Beach, Lovely Seaside Home

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

8.4 out of 10, Very good, (27)
"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!

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

10.0 out of 10, Exceptional, (67)
"The property is exceptional. Great location, clean, lots of space for our large group. It had everything we needed including ample parking in the back of the building. Maya is a wonderful host and was very accommodating with our requests. I would stay here again in a heartbeat."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
10.0 out of 10, Exceptional, (21)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is £566
includes taxes & fees
6 Oct - 7 Oct
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus

9.4 out of 10, Exceptional, (44)
"Very clean, comfortable, with cute decor. 3 minute walk from an excellent bakery and coffee shop that serves breakfast sandwiches, we walked there every morning. Also close to the beach. Neighborhood was quiet. "
The price is £506
includes taxes & fees
21 Sept - 22 Sept
*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus
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

Find out more about Massachusetts

Find out more about Massachusetts

Massachusetts Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in Massachusetts?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in Massachusetts?

Choose from 6639 beautiful holiday homes in Massachusetts for your getaway.


How much is a holiday home in Massachusetts?

You can find perfect holiday homes in Massachusetts for as low as £101 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Massachusetts?

Find the best deals on Massachusetts holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Massachusetts?

There’s no better way to spend your well-earned holiday than in a private, cosy Massachusetts holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Massachusetts.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Massachusetts holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Massachusetts—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Massachusetts car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Massachusetts Holiday Homes information

Number of reviews
1,125
Accommodation
6639 Holiday Homes
Lowest Price
£101
Highest Price
£794

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Explore a world of travel with Expedia