Massachusetts holiday rentals

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Latest Massachusetts holiday rental deals

MOST POPULARBoston
Holiday homes from €70

Best Massachusetts holiday rentals

Private, Spacious & Comfy 1 bedroom Entire Suite With Separate Entry & Free Parking - Holbrook - Bedroom
Private, Spacious & Comfy 1 bedroom Entire Suite With Separate Entry & Free Parking
Holbrook, MA, United States
8.2Very Good(27)
House
Parking
Free Wi-Fi
Air conditioning
€119+
Check availability
Weymouth Apartment Close to Beaches and Boston! - Weymouth - Living room
Weymouth Apartment Close to Beaches and Boston!
Weymouth, MA, United States
10Wonderful(7)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€205+
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
9.7Wonderful(30)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€393+
Check availability
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(5)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€189+
Check availability
The Cottages at Nantucket Boat Basin - Nantucket - Living room
The Cottages at Nantucket Boat Basin
Nantucket, MA, United States
9.4Wonderful(206)
Cottage
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€812+
Check availability
Global Luxury Suites East Boston - Boston - Lounge
Global Luxury Suites East Boston
East Boston
6.7Okay(209)
Apartment
Free Wi-Fi
Pool
Pet friendly
Air conditioning
€162+
Check availability
Park view South of Boston - Quincy - Quincy
Park view South of Boston - Quincy
Quincy, MA, United States
8.5Very Good(31)
Apartment
Parking
Free Wi-Fi
Air conditioning
€128+
Check availability
The Charles-South Shore - Randolph
The Charles-South Shore
Randolph, MA, United States
8.8Very Good(7)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€598+
Check availability
Harmony Medical Suites Chinatown - Boston
Harmony Medical Suites Chinatown
Chinatown
8.5Very Good(21)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€159+
Check availability
Global Luxury Suites at Kendall West - Cambridge
Global Luxury Suites at Kendall West
East Cambridge
10Wonderful(113)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€291+
Check availability
Boston Queen Bedroom - Boston
Boston Queen Bedroom
Dorchester
8.3Very Good(171)
Apartment
Free Wi-Fi
Air conditioning
€77+
Check availability
Beautiful 3br 3ba Duplex Parking Best Location Boston - Boston
Beautiful 3br 3ba Duplex Parking Best Location Boston
North End
10Wonderful(24)
Apartment
Free Wi-Fi
Air conditioning
€694+
Check availability
Charming Harvard Victorian - Cambridge
Charming Harvard Victorian
West Cambridge
8.2Very Good(29)
Apartment
Parking
Free Wi-Fi
Air conditioning
€715+
Check availability
Global Luxury Suites At Kendall East - Cambridge
Global Luxury Suites At Kendall East
East Cambridge
7.2Good(15)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€266+
Check availability
2 bedroom Boston condo in Jamaica Plain with parking - Boston
2 bedroom Boston condo in Jamaica Plain with parking
Jamaica Plain
8.8Very Good(10)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€296+
Check availability
Global Luxury Suites in South End - Boston
Global Luxury Suites in South End
South End
7.9Good(165)
Apartment
Free Wi-Fi
Pool
Pet friendly
Air conditioning
€200+
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 18 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
€244
€265
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 41% 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 March and May.
  • The cheapest night for renting a holiday home in Massachusetts is Friday. 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.
  • Pool, hot tub, parking, air-conditioned, 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.
  • The city in Massachusetts with the most affordable holiday homes is Boston, with around 1,331 properties and an average price of €73. The most popular holiday rentals in Massachusetts among KAYAK users are HomeStay in Boston - Dorchester Fields Corner Area, Homestay - Quiet bedroom near Harvard, and Homestay - A Home Away From Home.

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 (92% of total searches to Massachusetts). The next most popular destinations are Cambridge (4%) and Sturbridge (4%).

  • 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 €66. 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 €509.

  • 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 €2,182.

  • 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, condos, houses, homestays, boats, cabins, cottages, farm stays, houseboats, lodges, villas, agritourism, caravans, campgrounds, bungalows, bed & breakfasts and campsites.

  • 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 Sturbridge Route 20.

  • What are the most popular Massachusetts holiday rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated holiday home that can sleep 6 people or more by KAYAK users is Beach & King Street Inn.

  • 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.

Everything you need to know for your stay in Massachusetts

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