Massachusetts holiday rentals

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Best Massachusetts holiday rentals

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)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 1,215+
Check availability
74R - 2BR Quincy - Romantic Stay near Wollaston Beach - Quincy - Dining room
74R - 2BR Quincy - Romantic Stay near Wollaston Beach
Quincy, MA, United States
8.5Very Good(8)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 1,161+
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
AED 2,613+
Check availability
37 - 3BR Quincy - Cozy Townhouse near Adams Park - Quincy - Living room
37 - 3BR Quincy - Cozy Townhouse near Adams Park
Quincy, MA, United States
9.1Wonderful(42)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 1,587+
Check availability
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub - Weymouth - Living room
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Weymouth, MA, United States
Cottage
Free Wi-Fi
Air conditioning
AED 1,964+
Check availability
Weymouth Waterfront Getaway with Swim Spa and Hot Tub - Weymouth - Pool
Weymouth Waterfront Getaway with Swim Spa and Hot Tub
Weymouth, MA, United States
9.3Wonderful(18)
House
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
AED 1,818+
Check availability
Stunning beautiful and gorgeous Townhome 15 mins to Downtown Boston! - Quincy - Kitchen
Stunning beautiful and gorgeous Townhome 15 mins to Downtown Boston!
Quincy, MA, United States
9.2Wonderful(22)
House
Free Wi-Fi
Air conditioning
AED 1,759+
Check availability
Newly Renovated Open-Concept living space, close to Boston, plenty of parking - Milton - Dining room
Newly Renovated Open-Concept living space, close to Boston, plenty of parking
Milton, MA, United States
9.3Wonderful(3)
House
Free Wi-Fi
Air conditioning
AED 1,237+
Check availability
10-Spacious apt 5BR with gym, games room in the attic - Milton - Living room
10-Spacious apt 5BR with gym, games room in the attic
Milton, MA, United States
9.8Wonderful(12)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 1,870+
Check availability
Holmes Modern Homes - Quincy - Bedroom
Holmes Modern Homes
Quincy, MA, United States
House
Free Wi-Fi
Air conditioning
AED 602+
Check availability
Next to Boston & Beach, King Beds, Free Parking+EV - Quincy - Dining room
Next to Boston & Beach, King Beds, Free Parking+EV
Quincy, MA, United States
9.8Wonderful(11)
Condo
Free Wi-Fi
Air conditioning
AED 1,498+
Check availability
Modern Furnished Apartment in Heart of Quincy - Quincy
Modern Furnished Apartment in Heart of Quincy
Quincy, MA, United States
8.8Very Good(5)
Apartment
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
AED 999+
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
AED 1,278+
Check availability
Charming Harvard Victorian - Cambridge
Charming Harvard Victorian
West Cambridge
8.2Very Good(29)
Apartment
Parking
Free Wi-Fi
Air conditioning
AED 1,674+
Check availability
Boston Queen Bedroom - Boston
Boston Queen Bedroom
Dorchester
8.4Very Good(169)
Apartment
Free Wi-Fi
Air conditioning
AED 264+
Check availability
Temple Place Suites 2+3 - Boston
Temple Place Suites 2+3
Downtown
7.4Good(350)
Apartment
Free Wi-Fi
Air conditioning
AED 465+
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
April
AED 1,114
AED 1,284
Cheapest month to stay with an average 47% drop in price.
Most expensive month to stay with an average 87% 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 September and June.
  • The cheapest night for renting a holiday home in Massachusetts is Tuesday. In contrast, the most expensive is Thursday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Massachusetts for 7 days.
  • Pool, parking, pet friendly, air-conditioned, 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.

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 AED 262. 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 AED 341 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, condos, houses, homestays, cabins, cottages, boats, farm stays, houseboats, lodges, villas, bungalows, agritourism and caravans.

  • 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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Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
7.0Good(847)
Apartment
Free Wi-Fi
Air conditioning
AED 470+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(366)
Free Wi-Fi
Air conditioning
AED 1,972+
Check availability

Everything you need to know for your stay in Massachusetts

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