Massachusetts holiday rentals

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Best Massachusetts holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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AED 165 - AED 1,017AED 1,017 - AED 1,866AED 1,866 - AED 2,714AED 2,714 - AED 3,563AED 3,563+ per night

Property type

ApartmentCondoHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Massachusetts

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Homestay in Boston - 5 Locations in the Greater Boston - Boston
Homestay in Boston - 5 Locations in the Greater Boston
Dorchester
8.6Very Good(578)
Homestay
Parking
Free Wi-Fi
Air conditioning
AED 356+
Check availability
Miranova Suites - Quincy
Miranova Suites
Quincy, MA, United States
6.7Okay(39)
Apartment
Free Wi-Fi
Air conditioning
AED 364+
Check availability
Boston Monadnock Properties - Boston
Boston Monadnock Properties
Dorchester
8.5Very Good(190)
Homestay
Free Wi-Fi
Air conditioning
AED 366+
Check availability
Easy Commute South Boston 4br 1bh Apt - Boston
Easy Commute South Boston 4br 1bh Apt
South Boston
7.1Good(50)
Apartment
Free Wi-Fi
Air conditioning
AED 393+
Check availability
Homestay - We have trees and grass! - Boston
Homestay - We have trees and grass!
West Roxbury
Homestay
AED 426+
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Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
7.0Good(847)
Apartment
Free Wi-Fi
Air conditioning
AED 463+
Check availability
Bay Village Suites - Boston - Bedroom
Bay Village Suites
Bay Village
5.9Fair(432)
Apartment
Free Wi-Fi
AED 475+
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Temple Place Suites - Boston - Bedroom
Temple Place Suites
Downtown
6.8Okay(1161)
Apartment
Free Wi-Fi
Air conditioning
AED 479+
Check availability
Maverick Suites at 28 Fenway - Boston - Bedroom
Maverick Suites at 28 Fenway
Fenway–Kenmore
Apartment
Air conditioning
AED 484+
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Temple Place Suites 2+3 - Boston
Temple Place Suites 2+3
Downtown
7.3Good(350)
Apartment
Free Wi-Fi
Air conditioning
AED 522+
Check availability
Suites At 143 Arlington Street - Boston
Suites At 143 Arlington Street
Bay Village
6.8Okay(108)
Apartment
Free Wi-Fi
AED 581+
Check availability
4BR 1BH Apt in South Boston near Old Harbor Beach - Boston
4BR 1BH Apt in South Boston near Old Harbor Beach
South Boston
7.3Good(31)
Apartment
Free Wi-Fi
Air conditioning
AED 588+
Check availability
Furnished Apartment in Downtown - Boston
Furnished Apartment in Downtown
Downtown
6.9Okay(350)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
AED 640+
Check availability
Global Luxury Suites East Boston - Boston - Lounge
Global Luxury Suites East Boston
East Boston
6.7Okay(206)
Apartment
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
AED 735+
Check availability
Global Luxury Suites Downtown Boston - Boston - Living room
Global Luxury Suites Downtown Boston
Chinatown
7.8Good(1033)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
AED 846+
Check availability
Luxury Bliss Boston - Cambridge
Luxury Bliss Boston
Cambridgeport
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
AED 3,570+
Check availability
Booking Insights

KAYAK’s insights for holiday rentals in Massachusetts

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Massachusetts with confidence.

How early should you book a vacation rental in Massachusetts?

Book at least 15 days before your stay begins to get the best price for your Massachusetts vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
October
AED 1,090
AED 1,416
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 29% 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 September and June.
  • The cheapest night for renting a holiday home in Massachusetts is Tuesday. In contrast, the most expensive is Thursday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Massachusetts for 7 days.
  • Pool, hot tub, parking, air-conditioned, and pet friendly are the most popular holiday rental property amenities in Massachusetts
  • Holiday rentals in Massachusetts are around 17% more expensive than hotels on average. Search here to compare prices for all accommodation types in Massachusetts.

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 426. 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 341 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 apartments, houses, condos, homestays, cabins, cottages, boats, farm stays, houseboats, lodges, villas, bungalows, agritourism and caravans.

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

    There are a number of dog and pet-friendly Massachusetts holiday rentals, with around 9% allowing you to bring your pet along with you.

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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Popular topics

Holiday rentals by topic

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Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
7.0Good(847)
Apartment
Free Wi-Fi
Air conditioning
AED 463+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(366)
Free Wi-Fi
Air conditioning
AED 1,972+
Check availability

Everything you need to know for your stay in Massachusetts

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