Massachusetts holiday rentals

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Latest Massachusetts holiday rental deals

MOST POPULARSalem
Holiday homes from £368
Boston
Holiday homes from £137

Best Massachusetts holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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£53 - £435£435 - £816£816 - £1,197£1,197 - £1,578£1,578+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Massachusetts

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Private Room in Everett - Everett
Private Room in Everett
Everett, MA, United States
6.7Okay(1)
Free Wi-Fi
Pet-friendly
Air conditioning
£82+
Check availability
Homestay - We have trees and grass! - Boston
Homestay - We have trees and grass!
West Roxbury
£84+
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Good Harbor Beach Apt.- 6/10 mile - Gloucester - Outdoor view
Good Harbor Beach Apt.- 6/10 mile
Gloucester, MA, United States
9.9Wonderful(37)
Free Wi-Fi
Pet-friendly
Air conditioning
£164+
Check availability
Medford Apartment Rental, 5 Mi to Downtown Boston - Medford - Bedroom
Medford Apartment Rental, 5 Mi to Downtown Boston
Medford, MA, United States
9.5Wonderful(13)
Free Wi-Fi
Air conditioning
£218+
Check availability
Meadowbrook Rd - Braintree - Dining room
Meadowbrook Rd
Braintree, MA, United States
8.7Very Good(10)
Parking
Free Wi-Fi
Air conditioning
£323+
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Bay Colony Vista - Provincetown - Building
Bay Colony Vista
Provincetown, MA, United States
8.4Very Good(39)
Air conditioning
£356+
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Cozy family Apt near casino, Boston City and airport with hassle free parking! - Everett - Living room
Cozy family Apt near casino, Boston City and airport with hassle free parking!
Everett, MA, United States
9.6Wonderful(5)
Free Wi-Fi
Air conditioning
£366+
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Dreamcatcher - Chatham - Living room
Dreamcatcher
Chatham, MA, United States
10Wonderful(1)
Air conditioning
£367+
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Newly Renovated Apartment In The Heart Of Edgartown On The Bike Path! - Edgartown - Living room
Newly Renovated Apartment In The Heart Of Edgartown On The Bike Path!
Edgartown, MA, United States
8.5Very Good(18)
Air conditioning
£370+
Check availability
Modern 1-bedroom apartment in private Edgartown neighborhood w/ tennis court - Edgartown - Living room
Modern 1-bedroom apartment in private Edgartown neighborhood w/ tennis court
Edgartown, MA, United States
Air conditioning
£371+
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Riviera Sunset - Chatham - Living room
Riviera Sunset
Chatham, MA, United States
8.5Very Good(17)
Air conditioning
£378+
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1710 Halloween Escape| 2Br House|Downtown+Parking - Salem - Building
1710 Halloween Escape| 2Br House|Downtown+Parking
Downtown
9.9Wonderful(36)
Air conditioning
£406+
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Long Beach-Gloucester-2 minute walk to Beach! Large yard & lush gardens. Pup ok - Gloucester - Living room
Long Beach-Gloucester-2 minute walk to Beach! Large yard & lush gardens. Pup ok
Gloucester, MA, United States
10Wonderful(13)
Free Wi-Fi
£456+
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Let us help you make Salem a place to remember! - Salem
Let us help you make Salem a place to remember!
Salem, MA, United States
10Wonderful(1)
Parking
Free Wi-Fi
Air conditioning
£625+
Check availability
Niles Beach House - Beach & Boston Skyline Views - Gloucester - Bedroom
Niles Beach House - Beach & Boston Skyline Views
Gloucester, MA, United States
8.0Very Good(1)
Air conditioning
£1,140+
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Majestic 1800s Stately Home On Chestnut Street. The Nathaniel West House! - Salem - Living room
Majestic 1800s Stately Home On Chestnut Street. The Nathaniel West House!
Downtown
9.8Wonderful(10)
Air conditioning
£1,355+
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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
£239
£298
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 20% 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 November and April.
  • The cheapest night for renting a holiday home in Massachusetts is Friday. In contrast, the most expensive is Wednesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Massachusetts for 3 days.
  • Pool, 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 28% more expensive than hotels on average. Search here to compare prices for all accommodation types in Massachusetts.
  • The city in Massachusetts with the most affordable holiday homes is Boston, with around 1,726 properties and an average price of £102. The most popular holiday rentals in Massachusetts among KAYAK users are Temple Place Suites, HomeStay B&B in Boston - 3 locations in Dorchester, and Homestay - We have trees and grass!.

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 (34% of total searches to Massachusetts). The next most popular destinations are Salem (31%) and Edgartown (7%). Searches for holida rentals in Nantucket (5%), Cambridge (5%) and Plymouth (3%) are also popular.

  • 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 £63. Search here for similar prices

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

    The average price for a weekly Massachusetts holiday rental found by KAYAK users in the last 2 weeks is £1,206.

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

    The average price for a monthly Massachusetts holiday rental found by KAYAK users in the last 2 weeks is £5,169.

  • 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, cottages, homestays, boats, cabins, farm stays, houseboats, lodges, villas, caravans, agritourism, campgrounds, bungalows, caravan parks, chalets and barns.

  • What are some of the most-loved holiday rentals available in Massachusetts?

    There are many types of properties available for Massachusetts holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Econo Lodge and Quarters On Dot By Thatch.

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

    There are a number of dog and pet-friendly Massachusetts holiday rentals, with around 15% 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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Bricco Suites - Boston - Bar
Bricco Suites
North End
8.6Very Good(1136)
Free Wi-Fi
Air conditioning
£210+
Check availability
Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
6.9Okay(835)
Free Wi-Fi
Air conditioning
£104+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(370)
Free Wi-Fi
Air conditioning
£393+
Check availability

Everything you need to know for your stay in Massachusetts

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