Holiday homes & rentals in Massachusetts - HomeToGo base64Hash Holiday homes & rentals in Massachusetts - HomeToGo

Holiday homes & rentals in Massachusetts

Find 40,994 available offers from 44 partners
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Top 15 Recommended holiday lettings in Massachusetts

Find your perfect holiday home, apartment or cottage in Massachusetts from just £83 per night!

Condo Salisbury
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with terrace, garden & barbeque

Salisbury, Essex County, Massachusetts
This waterside condo in Salisbury features a kitchen, garden, and space for seven, perfect for a family getaway.
from £284
per night
Outstanding(52 ratings)
from £284
per night
View deal
House Plymouth
House ∙ 16 guests ∙ 6 bedrooms

Fully equipped wonderful house with barbeque, terrace & garden | Suitable for remote work

Plymouth, Plymouth County, Massachusetts
This spacious house rental in Plymouth offers beach access, a garden, and a balcony, perfect for gatherings of up to 16 guests.
from £581
per night
Outstanding(41 ratings)
from £581
per night
View deal
Cottage Salisbury
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage with terrace & barbecue | Nature view

Salisbury, Essex County, Massachusetts
This cottage in Salisbury features a kitchen, balcony, and direct beach access, perfect for up to 8 guests by the water.
from £240
per night
Outstanding(23 ratings)
from £240
per night
View deal
House Chatham
House ∙ 8 guests ∙ 4 bedrooms

House with BBQ, terrace & garden

Chatham, Barnstable County, Massachusetts
This family-friendly house rental in Chatham features a fireplace, garden, kitchen, and parking for up to 8 guests.
from £348
per night
Outstanding(61 ratings)
from £348
per night
View deal
House Gloucester
House ∙ 7 guests ∙ 4 bedrooms

Holiday home with terrace, garden & barbecue | Perfect for remote work

Gloucester, Essex County, Massachusetts
This Gloucester house rental offers beach access, a garden, and a fireplace, perfect for a memorable getaway with pets.
from £241
per night
Outstanding(35 ratings)
from £241
per night
View deal
House South Dennis
House ∙ 14 guests ∙ 7 bedrooms

Child-friendly nice holiday home with barbecue, garden & terrace | Perfect for remote work

South Dennis, Dennis, Massachusetts
This house rental in South Dennis offers a fireplace, spa, kitchen, and a garden, perfect for families of up to 14.
from £368
per night
Excellent(27 ratings)
from £368
per night
View deal
House Harwich Port
House ∙ 11 guests ∙ 5 bedrooms

Family-friendly holiday home with garden, barbecue & terrace | Beach nearby | Perfect for remote work

Harwich Port, Harwich, Massachusetts
This house rental in Harwich Port accommodates 11 guests and features a garden, kitchen, fireplace, and family-friendly amenities.
from £624
per night
Outstanding(48 ratings)
from £624
per night
View deal
House North Chatham
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented holiday home with barbecue, terrace & garden | City view | Pet-friendly

North Chatham, Chatham, Massachusetts
This North Chatham house rental for 10 offers a garden, balcony, fireplace, and a kitchen, perfect for family getaways.
from £313
per night
Outstanding(82 ratings)
from £313
per night
View deal
House Dennis
House ∙ 12 guests ∙ 5 bedrooms

House with terrace, garden & barbecue | Perfect for remote work

Dennis, Dennis Town, Massachusetts
This house rental in Dennis offers beach access, a garden, and space for 12, making it perfect for family getaways.
from £350
per night
Outstanding(62 ratings)
from £350
per night
View deal
House Sandwich
House ∙ 20 guests ∙ 9 bedrooms

House with barbeque, private pool & garden | Nature view | Good for workation

Sandwich, Barnstable County, Massachusetts
This spacious house rental in Sandwich features a heated private pool, garden, and ample space for up to 20 guests.
from £527
per night
Outstanding(23 ratings)
from £527
per night
View deal
House Dennis Port
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly pleasant holiday home with terrace, garden & barbeque

Dennis Port, Dennis, Massachusetts
This family-friendly house rental in Dennis Port features a fireplace, kitchen, garden, and parking, perfect for your getaway.
from £221
per night
Outstanding(27 ratings)
from £221
per night
View deal
House Wellfleet
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped ample holiday home with terrace & barbeque | Nature view | Close to the beach | Suitable for remote work | Pet-friendly

Wellfleet, Barnstable County, Massachusetts
This waterside house in Wellfleet offers beach access, a balcony, and space for seven, making it ideal for your next getaway.
from £431
per night
Excellent(45 ratings)
from £431
per night
View deal
House Oak Bluffs
House ∙ 12 guests ∙ 5 bedrooms

Family-oriented wonderful house with terrace & BBQ

Oak Bluffs, Dukes County, Massachusetts
This spacious house rental in Oak Bluffs features a fireplace, kitchen, and parking, perfect for family gatherings of up to 12.
from £643
per night
Outstanding(54 ratings)
from £643
per night
View deal
House Wellfleet
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with garden, terrace & barbecue | Nature view

Wellfleet, Barnstable County, Massachusetts
This Wellfleet house rental features a kitchen, garden, balcony, and parking, perfect for a family getaway with space for 6.
from £494
per night
Excellent(4 ratings)
from £494
per night
View deal
House Oak Bluffs
House ∙ 14 guests ∙ 7 bedrooms

Fully equipped wonderful holiday home with BBQ & terrace | City view | Close to the beach | Perfect for remote work

Oak Bluffs, Dukes County, Massachusetts
This Oak Bluffs house rental offers a kitchen, balcony, and parking, accommodating up to 14 guests for an unforgettable getaway.
from £1,217
per night
Outstanding(44 ratings)
from £1,217
per night
View deal

Holiday lettings and apartments with air conditioning

House  Edgartown
from £555 per night
House ∙ 10 guests ∙ 5 bedrooms

House with terrace & BBQ

4.8
Outstanding(44 ratings)
Edgartown, Dukes County, Massachusetts
Air conditioning
View deal
House  Vineyard Haven
from £426 per night
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented holiday home with garden, barbecue & terrace | Nature view | Suitable for remote work

5.0
Outstanding(26 ratings)
Vineyard Haven, Tisbury, Massachusetts
Air conditioning
View deal
House  East Sandwich
from £98 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with terrace & barbecue | Nature view | Perfect for remote work

5.0
Outstanding(22 ratings)
East Sandwich, Sandwich, Massachusetts
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  East Falmouth
from £808 per night
House ∙ 11 guests ∙ 4 bedrooms

Family-oriented holiday home with terrace, pool & BBQ | Close to the beach | Perfect for remote work

5.0
Outstanding(14 ratings)
East Falmouth, Falmouth, Massachusetts
Balcony/Patio
View deal
House  Wellfleet
from £530 per night
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped holiday home with BBQ, garden & terrace | Nature view | Next to the beach | Pets allowed

4.1
Very good(34 ratings)
Wellfleet, Barnstable County, Massachusetts
Balcony/Patio
View deal
House  West Dennis
from £403 per night
House ∙ 12 guests ∙ 6 bedrooms

House with barbecue & terrace | Nature view

5.0
Outstanding(36 ratings)
West Dennis, Dennis, Massachusetts
Balcony/Patio
View deal
See all offers

Most popular holiday lettings with a fireplace

Cottage  Brewster
from £157 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage with barbeque

Brewster, Brewster Town, Massachusetts
Fireplace
View deal
House  Chatham
from £121 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly pleasant house with terrace, BBQ & garden | Good for workation

5.0
Outstanding(24 ratings)
Chatham, Barnstable County, Massachusetts
Fireplace
View deal
House  Dennis Port
from £190 per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, terrace & barbecue

4.8
Outstanding(35 ratings)
Dennis Port, Dennis, Massachusetts
Fireplace
View deal
See all offers

Budget-friendly Holiday Homes in Massachusetts

Find Fantastic yet Cheap Lettings

Cottage Mattapoisett
from £176 per night
Cottage ∙ 7 guests ∙ 3 bedrooms

Cottage with garden, barbeque & terrace

4.8
Outstanding(61 ratings)
Mattapoisett, Plymouth County, Massachusetts
View deal
House Oak Bluffs
from £278 per night
House ∙ 4 guests ∙ 2 bedrooms

Children-friendly holiday home with terrace & barbecue

5.0
Outstanding(6 ratings)
Oak Bluffs, Dukes County, Massachusetts
View deal
House Edgartown
from £466 per night
House ∙ 14 guests ∙ 5 bedrooms

Children-friendly house with barbecue, terrace & private pool | City view | Suitable for remote work | Dogs allowed

5.0
Outstanding(49 ratings)
Edgartown, Dukes County, Massachusetts
View deal

Top-Rated Lettings and Properties in Massachusetts

Book Holiday Letting Offers with the Highest User Rating

House Hyannis
from £150 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque, garden & terrace | City view

4.9
Outstanding(80 ratings)
Hyannis, Barnstable, Massachusetts
View deal
House Dennis Port
from £408 per night
House ∙ 9 guests ∙ 4 bedrooms

Ample holiday home with pool & barbecue | Pet-friendly

5.0
Outstanding(27 ratings)
Dennis Port, Dennis, Massachusetts
View deal
House West Chatham
from £208 per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly holiday home with terrace, barbecue & garden | City view

4.7
Excellent(26 ratings)
West Chatham, Chatham, Massachusetts
View deal

Discover real guest reviews to help you choose the perfect stay in Massachusetts

How are reviews collected?
Mary H.
Guest verified by HomeToGo

Beautiful home perfect for a large family gathering. The kitchen was well stocked. We took advantage of the hot tub, piano, puzzle table, and playing games on the large dining table. Cross country skiing was available right outside the door and downhill a short drive away. Thanking you for making such a special time possible.

Reviewed on 22/01/2026 | Family
House Stockbridge
from £565 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Stockbridge, Berkshire County, Massachusetts
View deal
Jo-Ellen K.
Guest verified by HomeToGo

The house was clean and thoughtfully decorated. The grounds were beautiful. We had what we needed and were comfortable. The only downside was the step stairs which we didn’t discover until we arrived but we made do.

Reviewed on 29/10/2025 | Couple
Cottage Northfield
-10%
£115
from £103 per night
Cottage ∙ 2 guests ∙ 2 bedrooms
5.0
Outstanding(75 ratings)
Northfield, Franklin County, Massachusetts
View deal
John M.
Guest verified by HomeToGo

Area great for hiking, cycling or going to the coast. Tiny house very pleasant, hosts very accommodating. Had difficulty with GPS taking me to same address in address rather than Falmouth. Outside shower a bit surprising but works well.

Reviewed on 30/09/2025 | Couple
House East Falmouth
from £106 per night
House ∙ 2 guests ∙ 1 bedroom
4.5
Excellent(2 ratings)
East Falmouth, Falmouth, Massachusetts
View deal
Jeanette N.
Guest verified by HomeToGo

This lovely house is in a quiet neighborhood on the Cape Cod Canal. We had the nicest time. It's outfitted very well and is full of mementos from its original family, which we loved. Kitchen has everything you could need. We could easily have spent our time on the deck, the beach and in the water and never left and been perfectly happy. We did venture to Gilder beach (2 blocks from house) and had some other excursions. But being here was divine overall.

Reviewed on 18/08/2025 | Family
House Bourne
from £331 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(12 ratings)
Bourne, Barnstable County, Massachusetts
View deal
Joe S.
Guest verified by HomeToGo

The home is very spacious. Cupboards were well stocked with plates, bowls, etc. I received prompt replies to inquiries. The photos of the outside are deceiving, the deck and furniture were not maintained/cleaned. I didn't find a broom. There were no instructions for check out other than to take out the trash. A/C was blasting when we got there and we couldn't figure out how to regulate it (again, no instructions), so we turned it off and used the room units and fans. I did not find the coffee maker that I was told was there.

Reviewed on 07/07/2025 | Group
House North Eastham
from £257 per night
House ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(18 ratings)
North Eastham, Barnstable County, Massachusetts
View deal
Suzanne H.
Guest verified by HomeToGo

We came to stay here as a Mini honey moon and on first impressions it’s very sweet and romantic. And our only complaints would be that the beds were very uncomfortable and there was hair left in the shower drain.

Reviewed on 02/07/2025 | Couple
House Indian Lake East
from £180 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Indian Lake East, Worcester, Massachusetts
View deal
Christine C.
Guest verified by HomeToGo

The house was very nice, clean, and comfortable, the screened in porch was lovely, there was a great backyard with a fire-pit, and the road and neighborhood was quiet. WiFi worked great. The lake access was much closer than I thought, just a quick walk, great for kids that like to fish and swim. Roads were minimally traveled on and safe for kids to ride bikes. Nearby is a supermarket and a shopping center as well. We did not get to hike while we were there but it is clear that there is a ton of hiking nearby. All in all it was a great few days at a great house and I would highly recommend for a quiet getaway.

Reviewed on 24/09/2024 | Family
House Sherwood Forest
-7%
£143
from £132 per night
House ∙ 7 guests ∙ 2 bedrooms
4.7
Excellent(3 ratings)
Sherwood Forest, Becket, Massachusetts
View deal
Gail M.
Guest verified by HomeToGo

The location and home were both beautiful! We thoroughly enjoyed our stay! Rock Properties were very accommodating to any of our concerns and responded immediately! There was even a welcome basket with an assortment of Cape Cod gifts.

Reviewed on 14/05/2024 | Couple
House Sandwich
from £267 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Sandwich, Barnstable County, Massachusetts
View deal
William S.
Guest verified by HomeToGo

Found this hidden gem and couldn’t have been happier. We had our dog with us, who also had a great time. Place is very clean and the room had full amenities, which is rare (in my opinion). We had a full kitchen, tv with several streaming stations, and nice walk in shower. There was a pool out front and different hammocks and games out back. Very close to restaurants and beaches. Will definitely stay here again

Reviewed on 06/08/2023 | Couple
Accommodation Eastham
from £150 per night
Accommodation ∙ 2 guests ∙ 1 bedroom
4.6
Excellent(120 ratings)
Eastham, Orleans Town, Massachusetts
View deal
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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Massachusetts

  • Pool (10,447)
  • WiFi (37,161)
  • Parking (1,926)
  • Kitchen (24,951)
  • Air conditioning (36,247)
  • TV (35,790)
  • Dishwasher (17,375)
  • Washing machine (22,416)
  • Pet-friendly (12,655)
  • Wheelchair access (8,193)
  • No smoking (36,266)
  • Balcony/patio (15,342)

More than a quarter of the holiday rentals include a pool, which makes Massachusetts a wonderful holiday destination for travellers looking to spend their holidays poolside. More hotel room provide a pool than motel. On average, hotel room with pools in Massachusetts accommodate 9 holidaymakers and have an average cost of £447 per night. If you would also like to be near the water, more than half of the rentals including a pool are within 2 kilometres of the waterfront.

Price and Availability Index for Massachusetts

Click on any bar to see price and availability information

Holiday Letting Price Information in Massachusetts

We summarised price data in the graph above to give you more insights as to accommodation costs in Massachusetts. The most expensive week to book a holiday letting in Massachusetts is in July (04/07 – 11/07). The cheapest week is in February (14/02 – 21/02). Prices fall to an average of £500 per night.

Rental availability information in Massachusetts

Check how busy Massachusetts is with our availability graph. More people travel to Massachusetts during a week in January (16/01 – 23/01). So far, 98% of the Massachusetts holiday lettings are occupied this week. Conversely, 57% of the lettings are still available during a week in June (13/06 – 20/06).

Explore the diversity of Massachusetts with a holiday home

The state of Massachusetts was the site of the first colony in New England. Despite being a small state, there is a lot for travellers to do in Massachusetts. You can learn about fascinating historical events such as the Salem witch trials and the Boston Tea Party, or simply lounge on a Cape Cod beach.

When visiting Massachusetts, consider staying in one of the area’s many holiday lettings – they offer privacy and modern amenities, and they also feel like home.

Information about holiday rentals in Massachusetts

🏡 Holiday homes available 40,994 rentals
💳 Discounts available up to 18%
🌙 Nightly prices from £83
⭐ Popular amenities Pool, Internet and Parking
🐾 Pet friendly rentals 13,207 properties
🏊 Holiday rentals with pools 10,818 properties
222 reviews
Massachusetts holiday rentals have an average rating of 4.4/5 across 222 reviews left by travellers.

Frequently Asked Questions

What is the price per night for a holiday home in Massachusetts?

You can book a holiday home in Massachusetts for as little as £83 per night. Whether you're after something simple or more luxurious, there's a wide range available. Use HomeToGo to compare deals and find the best value for your trip.

How many holiday lettings are available to book in Massachusetts? And what are the most popular types of holiday lets?

There are 40,994 holiday apartments from 44 different providers on offer in Massachusetts. More than half of holiday rentals in Massachusetts are house rentals, making them a top pick among travellers. These properties are perfect for families, couples, or groups looking for a cosy base. Find your perfect match on HomeToGo today.

What is the most searched holiday apartment amenity in Massachusetts?

Travellers planning trips to Massachusetts most often look for Pool, Internet, and Parking as holiday rental amenities.

Do you offer holiday homes with a swimming pool in Massachusetts?

Looking for a pool? You’ll find that more than half of holiday cottages and homes in Massachusetts have one. They’re ideal for cooling off on sunny days or relaxing poolside, with 10,818 properties to choose from. Browse poolside holiday rentals on HomeToGo, starting from around £447.

What is the best time of year to travel to Massachusetts?

January and February are the driest months in Massachusetts.

How do I find deals on holiday lettings in Massachusetts?

You can find fabulous discounts on holiday lets in Massachusetts with the nightly price of a rental starting at just £83 - and HomeToGo has created a range of filters that mean it's a piece of cake to locate some awesome deals. When considering different dates for your break, you can use HomeToGo's flexible dates technology to scan for great value date options and find discounts of up to 18%. In addition, HomeToGo's 'distance from' filter can help you uncover hidden treasure holiday rentals in lower-price, lesser-known locales that are just as close to your desired destination, whether that's a beach, lake, ski region or city centre. Start searching with time to spare to get the best of good availability and top discounts - and do so without worries by using HomeToGo's 'free cancellation' filter when you search.

What are the advantages of choosing a holiday home in Massachusetts with HomeToGo?

From serenity away from the crowds to more space to enjoy with your family, friends or partner, holiday rentals in Massachusetts have a variety of benefits. HomeToGo surfaces real reviews from verified visitors, and searching is secure, simple, and hassle-free - so with 40,994 lettings from 44 providers in the region, you're bound to uncover the ideal holiday home with the amenities and features that are important to you in Massachusetts.

Do you offer holiday accommodation for couples in Massachusetts?

Absolutely – you’ll find plenty of cosy, well-rated holiday lettings in Massachusetts perfect for two. Whether you’re after seclusion or a city break, there’s something for every type of trip. Use HomeToGo to find the ideal spot for your next couples’ getaway.

Can I book a waterfront holiday rental in Massachusetts?

You can book one of 32218 waterfront holiday homes in Massachusetts for a truly scenic break. These spots are perfect for a morning coffee with a view or lazy days by the water. Filter your search by ‘Near water’ on HomeToGo to see your options.

Why should I book my holiday rental with HomeToGo?

HomeToGo brings together over 15 million holiday rentals from trusted providers, so you can find the best deal in one place. You’ll enjoy a simple booking process, local expertise, and top prices from trusted providers. Discover your ideal holiday home with ease on HomeToGo.

Can I find family-friendly holiday lettings in Massachusetts?

Yes, there are lots of family-friendly holiday homes in Massachusetts. Many come with space for large groups and practical features like kitchens and gardens. Use HomeToGo to discover the best places to stay with the whole gang.

Can I cancel my holiday rental booking for free?

Worried about changes? Plenty of holiday rentals listed on HomeToGo come with free cancellation options. Always read the terms to avoid surprises.

Is it possible to rent a holiday home for a weekend getaway in Massachusetts?

Yes, many holiday lets in Massachusetts offer flexible booking options, including weekend stays. You’ll find plenty of holiday homes that accept 2-3 night bookings. Discover your ideal holiday home with ease on HomeToGo.

Are there any last-minute holiday rental deals in Massachusetts?

Need a quick break? Last-minute holiday is just a few clicks away in Massachusetts. These can be a great way to save up to 18% on spontaneous getaways. Check today’s offers and grab a holiday cottage at a great price.

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