Massachusetts holiday rentals

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Best Massachusetts holiday rentals

Summer Village! Charming 2-bedroom cottage with AC, WiFi in delightful Westford - Westford - Kitchen
Summer Village! Charming 2-bedroom cottage with AC, WiFi in delightful Westford
Westford, MA, United States
10Wonderful(1)
Cottage
Air conditioning
R10 354+
Check availability
This apartment in Lowell is in a beautiful setting and part of our house. - Lowell - Building
This apartment in Lowell is in a beautiful setting and part of our house.
Lowell, MA, United States
10Wonderful(2)
Apartment
Air conditioning
R2 362+
Check availability
Blu Heaven a Place in Lakeville! Lakefront property - steps from water! - Lakeville - Living room
Blu Heaven a Place in Lakeville! Lakefront property - steps from water!
Lakeville, MA, United States
10Wonderful(2)
Lodge
Air conditioning
R8 528+
Check availability
Easy access! 1br, 5 min walk to T train, easy access to Highway - Westwood - Living room
Easy access! 1br, 5 min walk to T train, easy access to Highway
Westwood, MA, United States
8.9Very Good(11)
House
Free Wi-Fi
Air conditioning
R3 585+
Check availability
Modern Lake Home - 4-bedroom house in charming North Attleborough and Mansfield - North Attleboro - Dining room
Modern Lake Home - 4-bedroom house in charming North Attleborough and Mansfield
North Attleboro, MA, United States
House
Air conditioning
R12 616+
Check availability
Renovated 3 Bedroom Home with Family Theater Room and Sauna - Middleboro - Dining room
Renovated 3 Bedroom Home with Family Theater Room and Sauna
Middleboro, MA, United States
10Wonderful(4)
House
Air conditioning
R9 533+
Check availability
Apartments in Salem - Salem - Living room
Apartments in Salem
Downtown
8.0Very Good(90)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R4 406+
Check availability
Econo Lodge Sharon - Foxborough - Sharon - Bedroom
Econo Lodge Sharon - Foxborough
Sharon, MA, United States
6.6Okay(404)
Lodge
Parking
Free Wi-Fi
Air conditioning
R1 659+
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Brand new 4 bedroom high end home in Walpole - Walpole - Living room
Brand new 4 bedroom high end home in Walpole
Walpole, MA, United States
House
Air conditioning
R17 290+
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Home Away from Home! - Worcester - Balcony
Home Away from Home!
Worcester, MA, United States
9.1Wonderful(9)
House
Air conditioning
R6 618+
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Cozy 1br Getaway Near Downtown Worcester – Comfortable & Convenient Stay! - Worcester - Bedroom
Cozy 1br Getaway Near Downtown Worcester – Comfortable & Convenient Stay!
Worcester, MA, United States
10Wonderful(4)
Apartment
R3 652+
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Contemporary Style And Comfort Convenient To Boston And Route 128 - Dedham - Kitchen
Contemporary Style And Comfort Convenient To Boston And Route 128
Dedham, MA, United States
10Wonderful(23)
Apartment
Air conditioning
R1 659+
Check availability
1 Mi to Downtown Salem: Studio w/ Fire Pit Access - Salem - Bedroom
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
Salem, MA, United States
Apartment
Free Wi-Fi
Air conditioning
R5 311+
Check availability
Econo Lodge West Yarmouth on Cape Cod - West Yarmouth - Pool
Econo Lodge West Yarmouth on Cape Cod
West Yarmouth, MA, United States
6.8Okay(449)
Lodge
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 893+
Check availability
All-Season Sunroom and Fireplace! Chatham Getaway - Chatham - Dining room
All-Season Sunroom and Fireplace! Chatham Getaway
Chatham, MA, United States
8.4Very Good(4)
House
Free Wi-Fi
Air conditioning
R8 829+
Check availability
Gateway To Cape Cod Ada Accessible Cottage 6 - Rochester
Gateway To Cape Cod Ada Accessible Cottage 6
Rochester, MA, United States
7.7Good(9)
Campsite
Parking
Pool
Pet-friendly
Air conditioning
R2 949+
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
April
R5 298
R6 141
Cheapest month to stay with an average 52% drop in price.
Most expensive month to stay with an average 79% 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

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 R1 372. 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 R1 555 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, bed & breakfasts, agritourism, caravans and campgrounds.

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

    There are a number of dog and pet-friendly Massachusetts holiday rentals, with around 10% 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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Boston Christopher - Boston
Boston Christopher
South End
7.8Good(366)
Free Wi-Fi
Air conditioning
R8 997+
Check availability

Everything you need to know for your stay in Massachusetts

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