Massachusetts holiday rentals

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Best Massachusetts holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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£39 - £336£336 - £633£633 - £930£930 - £1,227£1,227+ per night

Property Types

ApartmentCondoCottageHomestayHouse

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Most recommended holiday rentals in Massachusetts

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Beverly, Salem, Dwtn, Water and Train - Beverly - Balcony
Beverly, Salem, Dwtn, Water and Train
Beverly, MA, United States
10Wonderful(1)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
£172+
Check availability
Moody Salem Home Away From Home - Salem - Bedroom
Moody Salem Home Away From Home
Salem, MA, United States
9.7Wonderful(50)
Apartment
Parking
Free Wi-Fi
Air conditioning
£196+
Check availability
Ocean Breeze-8min Walk to Beach - Gloucester - Living room
Ocean Breeze-8min Walk to Beach
Gloucester, MA, United States
9.7Wonderful(42)
Apartment
Parking
Free Wi-Fi
Air conditioning
£226+
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
£227+
Check availability
Salem Gem! Home away from home in Salem, Ma with yard! - Salem - Kitchen
Salem Gem! Home away from home in Salem, Ma with yard!
Salem, MA, United States
10Wonderful(1)
House
Air conditioning
£236+
Check availability
Walk to Downtown Salem with Arcade- Free Parking! - Salem
Walk to Downtown Salem with Arcade- Free Parking!
Salem, MA, United States
9.1Wonderful(9)
Apartment
Parking
Free Wi-Fi
Air conditioning
£236+
Check availability
1710 House|2Br Halloween Escape| Downtown+Parking - Salem - Building
1710 House|2Br Halloween Escape| Downtown+Parking
Downtown
9.9Wonderful(42)
Condo
Air conditioning
£239+
Check availability
Sea House - Chatham
Sea House
Chatham, MA, United States
9.0Wonderful(11)
House
£268+
Check availability
Lucky Number Seven - Chatham - Living room
Lucky Number Seven
Chatham, MA, United States
9.5Wonderful(64)
House
Pet-friendly
Air conditioning
£317+
Check availability
ii Serene 3-Bedroom Retreat in Charming Salem, MA - Salem - Living room
ii Serene 3-Bedroom Retreat in Charming Salem, MA
Salem, MA, United States
8.0Very Good(1)
Apartment
Air conditioning
£338+
Check availability
iii 3-Bedroom Penthouse Condo Retreat in Historical Salem, MA - Salem
iii 3-Bedroom Penthouse Condo Retreat in Historical Salem, MA
Salem, MA, United States
8.6Very Good(3)
Apartment
Air conditioning
£338+
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B By the Sea - Chatham - Living room
B By the Sea
Chatham, MA, United States
8.1Very Good(22)
House
Air conditioning
£401+
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NEW Robert Manning Place•Historic 1824 Salem Home with Parking•Walk to Downtown - Salem - Balcony
NEW Robert Manning Place•Historic 1824 Salem Home with Parking•Walk to Downtown
Salem, MA, United States
10Wonderful(15)
House
Free Wi-Fi
Air conditioning
£513+
Check availability
Cape Cod Villa - Harwich
Cape Cod Villa
Harwich, MA, United States
9.9Wonderful(12)
Villa
Parking
Free Wi-Fi
Air conditioning
£656+
Check availability
52 Union - Nantucket
52 Union
Nantucket, MA, United States
Villa
Parking
Free Wi-Fi
Air conditioning
£736+
Check availability
Luxury Dreamy Madaket Destination - Beachside, Ocean Views & Lifelong Memories - Nantucket - Living room
Luxury Dreamy Madaket Destination - Beachside, Ocean Views & Lifelong Memories
Nantucket, MA, United States
10Wonderful(1)
House
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£879+
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
£225
£289
Cheapest month to stay with an average 36% drop in price.
Most expensive month to stay with an average 29% 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 January.
  • The cheapest night for renting a holiday home in Massachusetts is Tuesday. 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 5 days.
  • The cheapest Massachusetts holiday rental found on KAYAK in the last 2 weeks was £395, while the most expensive was £395.
  • Pool, parking, air-conditioned, hot tub, and pet friendly 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.

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 (33% of total searches to Massachusetts). The next most popular destinations are Salem (25%) and Edgartown (6%). Searches for holida rentals in Cambridge (6%), Nantucket (5%) and Plymouth (4%) 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 £69. 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 £70 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, cottages, homestays, boats, cabins, farm stays, houseboats, lodges, villas, agritourism, caravans, campgrounds, bungalows 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 Quarters On Dot By Thatch and Econo Lodge West Yarmouth on Cape Cod.

  • 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.

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 - Restaurant
Bricco Suites
North End
8.6Very Good(1181)
Free Wi-Fi
Air conditioning
£156+
Check availability
Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
7.0Good(847)
Apartment
Free Wi-Fi
Air conditioning
£95+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(366)
Free Wi-Fi
Air conditioning
£406+
Check availability

Everything you need to know for your stay in Massachusetts