Massachusetts holiday rentals

Search hundreds of travel sites at once for holiday home deals in Massachusetts

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Best Massachusetts holiday rentals

Most recommended holiday rentals in Massachusetts

Show all
Lovely 2nd Floor Apartment - Greenfield - Living room
Lovely 2nd Floor Apartment
$342+
$342+
Shelburne Studio Cabin w/ Spring-Fed Pool! - Shelburne Falls - Kitchen
Shelburne Studio Cabin w/ Spring-Fed Pool!
9.3 Wonderful
$406+
$406+
Cozy Large House Close To Tufts/Harvard/Mit 4br - Medford - Bedroom
Cozy Large House Close To Tufts/Harvard/Mit 4br - Medford - Bedroom
Cozy Large House Close To Tufts/Harvard/Mit 4br
8.7 Very Good
$1,610+
$1,610+
Parking
Free Wi-Fi
Pet-friendly
RiverView: Walk to Train for Boston & Salem, Walk to Pubs & Shops, Spacious for Family Fun - Beverly - Bedroom
RiverView: Walk to Train for Boston & Salem, Walk to Pubs & Shops, Spacious for Family Fun - Beverly - Bedroom
RiverView: Walk to Train for Boston & Salem, Walk to Pubs & Shops, Spacious for Family Fun
$742+
$742+
Spacious Medford Gem - Medford - Living room
Spacious Medford Gem - Medford - Living room
Spacious Medford Gem
9.3 Wonderful
$584+
$584+
Parking
Free Wi-Fi
Lord Medford Apartments - Medford - Living room
Lord Medford Apartments - Medford - Living room
Lord Medford Apartments
9.5 Wonderful
$564+
$564+
Parking
Free Wi-Fi
Afternoon Delight: Toast the beauty of the river from the waterfront deck - Beverly
Afternoon Delight: Toast the beauty of the river from the waterfront deck - Beverly
Afternoon Delight: Toast the beauty of the river from the waterfront deck
$1,532+
$1,532+
Traveler's Den In Medford - Medford - Bedroom
Traveler's Den In Medford - Medford - Bedroom
Traveler's Den In Medford
9.2 Wonderful
$379+
$379+
Parking
Free Wi-Fi
Berkshire Vacation Rentals: Renovated Five Bedrooms In Historic Williamstown - Williamstown - Patio
Berkshire Vacation Rentals: Renovated Five Bedrooms In Historic Williamstown - Williamstown - Patio
Berkshire Vacation Rentals: Renovated Five Bedrooms In Historic Williamstown
$1,502+
$1,502+
Parking
Free Wi-Fi
Cozy House Stylish near Harvard Tufts w Parking - Medford - Living room
Cozy House Stylish near Harvard Tufts w Parking - Medford - Living room
Cozy House Stylish near Harvard Tufts w Parking
9.2 Wonderful
$1,558+
$1,558+
Free Wi-Fi
Pet-friendly
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St! - Williamstown - Building
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St! - Williamstown - Building
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
$1,648+
$1,648+
Pet-friendly
Moody Salem Home Away From Home - Salem - Bedroom
Moody Salem Home Away From Home - Salem - Bedroom
Moody Salem Home Away From Home
9.5 Wonderful
$469+
$469+
Parking
Free Wi-Fi
Dont Get Stucked In Boston Traffic - New Bedford - Living room
Dont Get Stucked In Boston Traffic - New Bedford - Living room
Dont Get Stucked In Boston Traffic
$1,272+
$1,272+
Parking
Free Wi-Fi
Pet-friendly
Stylish new 2 bedroom property in enchanting Shelburne Falls Village. - Shelburne Falls - Building
Stylish new 2 bedroom property in enchanting Shelburne Falls Village. - Shelburne Falls - Building
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
$474+
$474+
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36 - Brookline
A Stylish Stay w/ a Queen Bed, Heated Floors.. #36
8.1 Very Good
$409+
$409+
Free Wi-Fi
North Beverly Haven - Beverly
North Beverly Haven - Beverly
North Beverly Haven
$1,225+
$1,225+
Parking
Free Wi-Fi
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $353$353 - $707$707 - $1,060$1,060 - $1,412$1,412+ per night

Property type

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

March

High season

August

Average price (weeknight)

$492

Average price (weekend night)

$540
Cheapest month to stay with an average 22% drop in price.
Most expensive month to stay with an average 26% 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

See more tips

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 (48% of total searches to Massachusetts). The next most popular destinations are Cambridge (7%) and Edgartown (7%). Searches for holida rentals in Salem (7%), Mashpee (7%) and Eastham (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 $191. 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 $182 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 houses, homestays, lodges, apartments, condos, agritourism, caravans, cottages, houseboats, boats, cabins, chalets, farm stays, villas, campgrounds, barns, campsites, bungalows and caravan parks.

  • 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 Econo Lodge and Quarters On Dot By Thatch.

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

    There are a number of dog and pet-friendly Massachusetts holiday rentals, with around 14% allowing you to bring your pet along with you.

See more FAQs

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

Show all

Holiday rentals by topic

Show all
Quarters On Dot By Thatch - Boston - Room amenity
Quarters On Dot By Thatch
6.9 Okay
South Boston$225+
$225+
Free Wi-Fi
Boston Christopher - Boston
Boston Christopher
7.8 Good
South End$851+
$851+
Free Wi-Fi

Popular topics

Everything you need to know for your stay in Massachusetts

Complete your trip to Massachusetts

Flights to Massachusetts
Car hire in Massachusetts

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.