Massachusetts holiday rentals

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Best Massachusetts holiday rentals

Spacious Private Entrance Master Bedroom/Bath - Wellesley - Building
Spacious Private Entrance Master Bedroom/Bath
Wellesley, MA, United States
9.9Wonderful(52)
Apartment
Free Wi-Fi
Air conditioning
AED 581+
Check availability
Entire apartment with private entrance. - Chestnut Hill - Living room
Entire apartment with private entrance.
Chestnut Hill, MA, United States
9.3Wonderful(63)
Apartment
Air conditioning
AED 1,142+
Check availability
Lovely studio walk to Wellesley and Babson College - Wellesley - Bedroom
Lovely studio walk to Wellesley and Babson College
Wellesley, MA, United States
9.8Wonderful(29)
House
Air conditioning
AED 1,417+
Check availability
Beautiful home in Wellesley's Historic district - Wellesley - Bedroom
Beautiful home in Wellesley's Historic district
Wellesley, MA, United States
10Wonderful(9)
House
Air conditioning
AED 9,588+
Check availability
Elegant Guest Suite Wellesley - Wellesley - Dining room
Elegant Guest Suite Wellesley
Wellesley, MA, United States
10Wonderful(2)
House
Free Wi-Fi
Air conditioning
AED 1,373+
Check availability
Private Base, #Boston medical #Boston Collage, #The Country Club T+Prk - Chestnut Hill - Dining room
Private Base, #Boston medical #Boston Collage, #The Country Club T+Prk
Chestnut Hill, MA, United States
9.5Wonderful(64)
House
Free Wi-Fi
Air conditioning
AED 1,355+
Check availability
Cottage Suite 'B' - Walk to Shops, Train, History - Concord - Patio
Cottage Suite 'B' - Walk to Shops, Train, History
Concord, MA, United States
10Wonderful(4)
Apartment
Air conditioning
AED 951+
Check availability
Clean, Spacious And Located Steps Away From The Mbta! - Boston - Building
Clean, Spacious And Located Steps Away From The Mbta!
Brighton
10Wonderful(18)
Apartment
Air conditioning
AED 1,691+
Check availability
Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley - Wellesley - Dining room
Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley
Wellesley, MA, United States
10Wonderful(1)
House
Free Wi-Fi
Air conditioning
AED 1,436+
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Brighton 2 bedroom - Boston - Kitchen
Brighton 2 bedroom
Brighton
9.0Wonderful(3)
Apartment
Parking
Air conditioning
AED 1,661+
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Perfect Getaway In Historic Newtonhighland (Cdc Safe) - Newton - Bedroom
Perfect Getaway In Historic Newtonhighland (Cdc Safe)
Newton, MA, United States
8.7Very Good(18)
House
Free Wi-Fi
AED 1,050+
Check availability
Boston Single Family House - 19' Train to Back Bay - Boston - Balcony
Boston Single Family House - 19' Train to Back Bay
West Roxbury
9.8Wonderful(11)
House
Parking
Free Wi-Fi
Air conditioning
AED 4,173+
Check availability
Gorgeous 2nd Floor Home with Private Entry - Canton
Gorgeous 2nd Floor Home with Private Entry
Canton, MA, United States
Apartment
Parking
Free Wi-Fi
Air conditioning
AED 851+
Check availability
Brighton Apartment Sleeps 3 - Steps to Bus Line - Boston
Brighton Apartment Sleeps 3 - Steps to Bus Line
Brighton
8.4Very Good(16)
Apartment
Free Wi-Fi
Air conditioning
AED 583+
Check availability
Renovated, Spacious Studio, Near Bc, Bu, Porch - Chestnut Hill
Renovated, Spacious Studio, Near Bc, Bu, Porch
Chestnut Hill, MA, United States
7.6Good(14)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
AED 745+
Check availability
Homestay - We have trees and grass! - Boston
Homestay - We have trees and grass!
West Roxbury
Homestay
AED 426+
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 18 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 1,071
AED 1,211
Cheapest month to stay with an average 41% drop in price.
Most expensive month to stay with an average 39% 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 August.
  • The cheapest night for renting a holiday home in Massachusetts is Sunday. 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 23% 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 267. 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 270 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.

Everything you need to know for your stay in Massachusetts

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