Massachusetts Holiday Rentals – KAYAK

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Best Massachusetts holiday rentals

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R903 - R4 220 R4 220 - R7 519 R7 519 - R10 836 R10 836 - R14 135 R14 135+ per night

Property Types

Apartment Condo Cottage Homestay House

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Free cancellation Free breakfast Free parking Free internet

Homestay - We have trees and grass! - Boston

Homestay - We have trees and grass!

West Roxbury

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Quarters On Dot By Thatch - Boston

Quarters On Dot By Thatch

South Boston

Free Wi-Fi

Air conditioning

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HomeStay B&B in Boston - 3 locations in Dorchester - Boston

HomeStay B&B in Boston - 3 locations in Dorchester

Dorchester

8.6Very Good(500)

Parking

Free Wi-Fi

Air conditioning

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Bay Village Suites - Boston

Bay Village Suites

Bay Village

Free Wi-Fi

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Temple Place Suites 2+3 - Boston

Temple Place Suites 2+3

Downtown

Free Wi-Fi

Air conditioning

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Temple Place Suites - Boston - Bedroom

Temple Place Suites

Downtown

Free Wi-Fi

Air conditioning

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1 Mi to Downtown Salem Vacation Rental! - Salem - Patio

1 Mi to Downtown Salem Vacation Rental!

Salem, MA, United States

9.1Wonderful(24)

Free Wi-Fi

Pet-friendly

Air conditioning

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Down Town Salem brand-new 1bdr apt

Salem, MA, United States

10Wonderful(16)

Air conditioning

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Global Luxury Suites Downtown Boston - Boston - Lobby

Global Luxury Suites Downtown Boston

Chinatown

Free Wi-Fi

Pet-friendly

Air conditioning

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Apartments in Salem - Salem - Living room

Apartments in Salem

Downtown

8.5Very Good(86)

Parking

Free Wi-Fi

Pet-friendly

Air conditioning

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Salem 3rd Floor 3br Apartment - Salem - Bedroom

Salem 3rd Floor 3br Apartment

Downtown

9.1Wonderful(7)

Air conditioning

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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

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Witch City Retreat with Tiki Bar in Downtown Salem - Salem - Building

Witch City Retreat with Tiki Bar in Downtown Salem

Salem, MA, United States

Parking

Free Wi-Fi

Pet-friendly

Air conditioning

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New! Family-Friendly Getaway -1 Mi To Dtwn Salem! - Salem

New! Family-Friendly Getaway -1 Mi To Dtwn Salem!

Salem, MA, United States

9.2Wonderful(24)

Parking

Pet-friendly

Air conditioning

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Artistic Historical home, walkDT - Salem - Living room

Artistic Historical home, walkDT

Downtown

10Wonderful(18)

Parking

Free Wi-Fi

Air conditioning

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The Cottages at Nantucket Boat Basin - Nantucket - Living room

The Cottages at Nantucket Boat Basin

Nantucket, MA, United States

9.3Wonderful(200)

Parking

Free Wi-Fi

Pet-friendly

Air conditioning

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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.

Low season	High season	Average price (weeknight)	Average price (weekend night)
January	June	R5 678	R7 037
Cheapest month to stay with an average 40% drop in price.	Most expensive month to stay with an average 15% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

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 June and April.
The cheapest night for renting a holiday home in Massachusetts is Tuesday. In contrast, the most expensive is Saturday.
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 14% more expensive than hotels on average. Search here to compare prices for all accommodation types in Massachusetts.

What is the most popular holiday rental destination in Massachusetts?
Based on KAYAK holiday rental searches, the most popular destination is Boston (92% of total searches to Massachusetts). The next most popular destination is Chatham (8%).
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 590. 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, cottages, cabins, boats, farm stays, houseboats, lodges, villas, bungalows, agritourism, caravan parks, chalets, barns, 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 15% allowing you to bring your pet along with you.

What Massachusetts holiday rental guests are talking about

Popular topics

Boston Christopher - Boston

Boston Christopher

South End

Free Wi-Fi

Air conditioning

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Everything you need to know for your stay in Massachusetts

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