Massachusetts holiday rentals

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Best Massachusetts holiday rentals

Most recommended holiday rentals in Massachusetts

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Beautiful home in Wellesley's Historic district - Wellesley - Bedroom
Beautiful home in Wellesley's Historic district
AED 10,705+
AED 10,705+
Air conditioning
Spacious Private Entrance Master Bedroom/Bath - Wellesley - Building
Spacious Private Entrance Master Bedroom/Bath
9.9 Wonderful
AED 632+
AED 632+
Free Wi-Fi
Air conditioning
Dreamy Somerville 2BR w/ W/D, near Union Square T Stop - Somerville - Living room
Dreamy Somerville 2BR w/ W/D, near Union Square T Stop - Somerville - Living room
Dreamy Somerville 2BR w/ W/D, near Union Square T Stop
AED 683+
AED 683+
Air conditioning
4BDR Near Tufts-10min-Walk to Subway-Free Parking - Somerville - Living room
4BDR Near Tufts-10min-Walk to Subway-Free Parking - Somerville - Living room
4BDR Near Tufts-10min-Walk to Subway-Free Parking
AED 970+
AED 970+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Lakefront private house secluded yet close to everything 3bed 2bath w gameroom! - Natick - Living room
Lakefront private house secluded yet close to everything 3bed 2bath w gameroom! - Natick - Living room
Lakefront private house secluded yet close to everything 3bed 2bath w gameroom!
AED 2,824+
AED 2,824+
Air conditioning
Cozy Large House Close To Tufts/Harvard/Mit 4br - Medford - Bedroom
Cozy Large House Close To Tufts/Harvard/Mit 4br - Medford - Bedroom
Cozy Large House Close To Tufts/Harvard/Mit 4br
8.7 Very Good
AED 3,796+
AED 3,796+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Spacious Medford Gem - Medford - Living room
Spacious Medford Gem - Medford - Living room
Spacious Medford Gem
9.3 Wonderful
AED 1,355+
AED 1,355+
Parking
Free Wi-Fi
Air conditioning
Sunny Dog Friendly Union Sq 1brm - Somerville - Living room
Sunny Dog Friendly Union Sq 1brm - Somerville - Living room
Sunny Dog Friendly Union Sq 1brm
AED 1,132+
AED 1,132+
Air conditioning
Lord Medford Apartments - Medford - Living room
Lord Medford Apartments - Medford - Living room
Lord Medford Apartments
9.5 Wonderful
AED 1,309+
AED 1,309+
Parking
Free Wi-Fi
Air conditioning
Cozy Somerville Studio 2 Mi to Boston, Walk to T! - Somerville - Bedroom
Cozy Somerville Studio 2 Mi to Boston, Walk to T! - Somerville - Bedroom
Cozy Somerville Studio 2 Mi to Boston, Walk to T!
9.3 Wonderful
AED 818+
AED 818+
Free Wi-Fi
Pet-friendly
Air conditioning
Traveler's Den In Medford - Medford - Bedroom
Traveler's Den In Medford - Medford - Bedroom
Traveler's Den In Medford
9.2 Wonderful
AED 878+
AED 878+
Parking
Free Wi-Fi
Air conditioning
Cozy Third-Story Apartment in Dtwn Brockton! - Brockton - Building
Cozy Third-Story Apartment in Dtwn Brockton! - Brockton - Building
Cozy Third-Story Apartment in Dtwn Brockton!
9.2 Wonderful
AED 735+
AED 735+
Free Wi-Fi
Pet-friendly
Air conditioning
Cozy House Stylish near Harvard Tufts w Parking - Medford - Living room
Cozy House Stylish near Harvard Tufts w Parking - Medford - Living room
Cozy House Stylish near Harvard Tufts w Parking
9.2 Wonderful
AED 3,574+
AED 3,574+
Free Wi-Fi
Pet-friendly
Air conditioning
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36
8.1 Very Good
AED 1,009+
AED 1,009+
Free Wi-Fi
Air conditioning
Luxe 4br 3 Bath North End & Faneuil Hall - Somerville
Luxe 4br 3 Bath North End & Faneuil Hall - Somerville
Luxe 4br 3 Bath North End & Faneuil Hall
AED 419+
AED 419+
Free Wi-Fi
Pet-friendly
A Stylish Stay w/ a Queen Bed, Heated Floors.. #31 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #31 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #31
8.4 Very Good
AED 1,051+
AED 1,051+
Free Wi-Fi
Air conditioning
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AED 0 - AED 2,571AED 2,571 - AED 5,142AED 5,142 - AED 7,712AED 7,712 - AED 10,283AED 10,283+ per night

Property type

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

April

High season

July

Average price (weeknight)

AED 1,163

Average price (weekend night)

AED 1,245
Cheapest month to stay with an average 15% drop in price.
Most expensive month to stay with an average 32% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Massachusetts holiday rental

  • If you’re looking for a cheap holiday rental in Massachusetts, you should consider visiting during the low season. The cheapest holiday homes in Massachusetts can be found in August and July.
  • The cheapest night for renting a holiday home in Massachusetts is Wednesday. In contrast, the most expensive is Friday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Massachusetts for 4 days.
  • Pool, kitchen/kitchenette, pet friendly, air-conditioned, airport shuttle, and hot tub are the most popular holiday rental property amenities in Massachusetts
  • Holiday rentals in Massachusetts are around 23% more expensive than hotels on average. Search here to compare prices for all accommodation types in Massachusetts.
See more tips

FAQs when booking a holiday home in Massachusetts

  • What is the most popular holiday rental destination in Massachusetts?

    Based on KAYAK holiday rental searches, the most popular destination is Boston (100% of total searches to Massachusetts).

  • How much is a holiday rental in Massachusetts for tonight?

    In the last 72 hours, users have found Massachusetts holiday rentals for tonight for as little as AED 406. Search here for similar prices

  • How much is a holiday rental in Massachusetts for this weekend?

    In the last 72 hours, users have found Massachusetts holiday rentals for this weekend for as little as AED 422 per night. Search here for similar prices

  • What types of holiday rentals are available in Massachusetts?

    There are loads of different property types that you can make your holiday home in Massachusetts. You’ll find houses, homestays, lodges, apartments, condos, cottages, houseboats, cabins, boats, chalets, farm stays, villas, campgrounds, agritourism, barns, campsites, bungalows and caravan parks.

  • Are there any pet-friendly holiday rentals in Massachusetts?

    There are a number of dog and pet-friendly Massachusetts holiday rentals, with around 14% allowing you to bring your pet along with you.

See more FAQs

Where to stay in Massachusetts?

Our map will help you find the perfect place to stay in Massachusetts by showing you the exact location of each holiday home.

What Massachusetts holiday rental guests are talking about

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Holiday rentals by topic

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Quarters On Dot By Thatch - Boston - Room amenity
Quarters On Dot By Thatch
6.9 Okay
South BostonAED 528+
AED 528+
Free Wi-Fi
Air conditioning
Boston Christopher - Boston
Boston Christopher
7.8 Good
South EndAED 1,972+
AED 1,972+
Free Wi-Fi
Air conditioning

Popular topics

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