Massachusetts holiday rentals

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Latest Massachusetts holiday rental deals

MOST POPULARBoston
Holiday homes from €74

Best Massachusetts holiday rentals

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€55 - €216€216 - €375€375 - €534€534 - €694€694+ per night

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Most recommended holiday rentals in Massachusetts

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Picon Homey - Springfield - Living room
Picon Homey
Springfield, MA, United States
6.5Okay(49)
Parking
Free Wi-Fi
Air conditioning
€125+
Check availability
Thompson Extended Stay- Close to everything. Large yard to unwind. - Springfield - Patio
Thompson Extended Stay- Close to everything. Large yard to unwind.
Springfield, MA, United States
Air conditioning
€160+
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Cozy 3-Beds in 2-Bedrooms Apartment Near Quincy Adams - Quincy - Bedroom
Cozy 3-Beds in 2-Bedrooms Apartment Near Quincy Adams
Quincy, MA, United States
10Wonderful(3)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€196+
Check availability
Cozy Springfield Apartment, Close to Parks! - Springfield - Living room
Cozy Springfield Apartment, Close to Parks!
Springfield, MA, United States
9.5Wonderful(9)
Free Wi-Fi
Air conditioning
€218+
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Bright Springfield Apartment with 2 Balconies! - Springfield - Living room
Bright Springfield Apartment with 2 Balconies!
Springfield, MA, United States
9.2Wonderful(11)
Free Wi-Fi
Air conditioning
€221+
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Cozy Cape Condo - Provincetown
Cozy Cape Condo
Provincetown, MA, United States
8.0Very Good(2)
€261+
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74R - 2BR Quincy - Romantic Stay near Wollaston Beach - Quincy - Dining room
74R - 2BR Quincy - Romantic Stay near Wollaston Beach
Quincy, MA, United States
10Wonderful(3)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€316+
Check availability
74L - 2BR Quincy - Cozy Couple Hideout near Wollaston Beach - Quincy - Dining room
74L - 2BR Quincy - Cozy Couple Hideout near Wollaston Beach
Quincy, MA, United States
9.5Wonderful(2)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€316+
Check availability
The Place to be... - Provincetown
The Place to be...
Provincetown, MA, United States
8.2Very Good(12)
€351+
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Endless Summer - Provincetown
Endless Summer
Provincetown, MA, United States
9.0Wonderful(25)
€359+
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Cape Point Escape - Provincetown
Cape Point Escape
Provincetown, MA, United States
8.3Very Good(7)
€360+
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Long Point Getaway - Provincetown - Beach
Long Point Getaway
Provincetown, MA, United States
9.4Wonderful(24)
Free Wi-Fi
Air conditioning
€388+
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383 - 3BR Quincy - Chic House near Adams Park - Quincy - Kitchen
383 - 3BR Quincy - Chic House near Adams Park
Quincy, MA, United States
10Wonderful(15)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€393+
Check availability
37 - 3BR Quincy - Cozy Townhouse near Adams Park - Quincy
37 - 3BR Quincy - Cozy Townhouse near Adams Park
Quincy, MA, United States
9.1Wonderful(39)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€438+
Check availability
555-2 6BR Quincy - Spacious Apt near Perry Beach - Quincy - Living room
555-2 6BR Quincy - Spacious Apt near Perry Beach
Quincy, MA, United States
9.8Wonderful(25)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€673+
Check availability
284 - 5BR Boston - Peaceful House near England Aqua - Quincy - Living room
284 - 5BR Boston - Peaceful House near England Aqua
Quincy, MA, United States
9.7Wonderful(56)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€675+
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
€284
€338
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 3% 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 May and October.
  • The cheapest night for renting a holiday home in Massachusetts is Saturday. In contrast, the most expensive is Sunday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Massachusetts for 1 days.
  • The cheapest Massachusetts holiday rental found on KAYAK in the last 2 weeks was €116, while the most expensive was €116.
  • 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 25% 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 1,725 properties and an average price of €63. 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 (78% of total searches to Massachusetts). The next most popular destinations are Salem (6%) and Nantucket (6%). Searches for holida rentals in Hyannis (3%), Cambridge (3%) and Gloucester (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 €73. 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 €73 per night. 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 €441.

  • 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 €1,891.

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

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

    If you’re looking for something special, the holiday rental most loved by KAYAK users is 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 14% 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
6.9Okay(835)
Free Wi-Fi
Air conditioning
€120+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(370)
Free Wi-Fi
Air conditioning
€458+
Check availability

Everything you need to know for your stay in Massachusetts

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