Massachusetts vacation rentals

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Best Massachusetts vacation rentals

Most recommended vacation rentals in Massachusetts

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Brimfield Waterfront cottage - Brimfield - Living room
Brimfield Waterfront cottage
Brimfield, MA, United States
₱16,168+
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Cozy Large House Close To Tufts/Harvard/Mit 4br - Medford - Bedroom
Cozy Large House Close To Tufts/Harvard/Mit 4br
Medford, MA, United States
8.7Very good(6)
Parking
Free Wi-Fi
Pet friendly
₱41,045+
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Stockbridge Home Walk to Town Beach! - Stockbridge - Living room
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.1Wonderful(8)
Free Wi-Fi
₱18,034+
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Mansion Wifi Fire Pit Sleeps 14 - Dedham - Living room
Mansion Wifi Fire Pit Sleeps 14
Dedham, MA, United States
Free Wi-Fi
Pet friendly
₱170,729+
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Stockbridge Vacation by Norman Rockwell - Stockbridge - Restaurant
Stockbridge Vacation by Norman Rockwell
Stockbridge, MA, United States
Pet friendly
₱18,995+
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Classic Stockbridge Cottage - Stockbridge - Building
Classic Stockbridge Cottage
Stockbridge, MA, United States
Parking
Free Wi-Fi
Pet friendly
₱27,810+
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Luxury Home, Pool, fireplace - Brimfield - Living room
Luxury Home, Pool, fireplace
Brimfield, MA, United States
₱66,651+
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In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing - Stockbridge - Living room
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
Stockbridge, MA, United States
Pet friendly
₱68,516+
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Econo Lodge Sturbridge Route 20 - Sturbridge - Bedroom
Econo Lodge Sturbridge Route 20
Sturbridge, MA, United States
6.4Okay(635)
Parking
Free Wi-Fi
Pet friendly
₱6,203+
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Spacious Medford Gem - Medford - Living room
Spacious Medford Gem
Medford, MA, United States
9.4Wonderful(19)
Parking
Free Wi-Fi
₱23,300+
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1780 Colonial Hilltop Manor - Amazing location - Stockbridge - Patio
1780 Colonial Hilltop Manor - Amazing location
Stockbridge, MA, United States
₱40,251+
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Historic Retreat - Stockbridge
Historic Retreat
Stockbridge, MA, United States
Parking
₱24,761+
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Escape To Stockbridge|ski & Explore|the Berkshires| - Stockbridge
Escape To Stockbridge|ski & Explore|the Berkshires|
Stockbridge, MA, United States
Free Wi-Fi
Pet friendly
₱40,816+
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Homestay - We have trees and grass! - Boston
Homestay - We have trees and grass!
West Roxbury
₱8,480+
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Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks - Lenox
Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks
Lenox, MA, United States
₱33,410+
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Charming 3BR Colonial Home in Wellesley - Wellesley
Charming 3BR Colonial Home in Wellesley
Wellesley, MA, United States
₱14,922+
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Good to know

Low season

January

High season

July

Average price (weeknight)

₱15,775

Average price (weekend night)

₱17,093
Cheapest month to stay with an average 20% drop in price.
Most expensive month to stay with an average 72% 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 vacation rental

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FAQs when booking a vacation home in Massachusetts

  • What is the most popular vacation rental destination in Massachusetts?

    Based on KAYAK vacation rental searches, the most popular destination is Salem (38% of total searches to Massachusetts). The next most popular destinations are Boston (38%) and Cambridge (25%).

  • How much is a vacation rental in Massachusetts for tonight?

    In the last 72 hours, users have found Massachusetts vacation rentals for tonight for as low as ₱4,657. Search here for similar prices

  • What types of vacation rentals are available in Massachusetts?

    There are loads of different property types that you can make your vacation home in Massachusetts. You’ll find houses, homestays, lodges, apartments, condos, houseboats, cottages, cabins, boats, chalets, farm stays, villas, campgrounds, agritourism, barns, holiday parks, bungalows and caravan parks.

  • Are there any pet-friendly vacation rentals in Massachusetts?

    There are a number of dog and pet-friendly Massachusetts vacation rentals, with around 16% allowing you to bring your pet along with you.

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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 vacation home.

What Massachusetts vacation rental guests are talking about

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Vacation rentals by topic

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Quarters On Dot By Thatch - Boston - Outdoors view
Quarters On Dot By Thatch
South Boston
6.9Okay(818)
Free Wi-Fi
₱9,992+
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Boston Christopher - Boston
Boston Christopher
South End
7.8Good(375)
Free Wi-Fi
₱30,358+
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