Massachusetts holiday rentals

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Best Massachusetts holiday rentals

Most recommended holiday rentals in Massachusetts

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Large relaxing house in 25 acres of private woods with lake access. - Spencer - Dining room
Large relaxing house in 25 acres of private woods with lake access.
Spencer, MA, United States
Free Wi-Fi
S$ 877+
Check availability
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 - Winchester - Dining room
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Winchester, MA, United States
Free Wi-Fi
S$ 251+
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Horse Heaven - Oxford - Bedroom
Horse Heaven
Oxford, MA, United States
S$ 652+
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Great Stay Two Beds Apartment In Harvard - Belmont - Living room
Great Stay Two Beds Apartment In Harvard
Belmont, MA, United States
S$ 347+
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5 bedrooms Home away from Home - Leicester - Living room
5 bedrooms Home away from Home
Leicester, MA, United States
9.8Wonderful(5)
S$ 942+
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Lovely Newton 2BR w/ W/D & Gym, nr Newtonville T, by Blueground - Boston - Living room
Lovely Newton 2BR w/ W/D & Gym, nr Newtonville T, by Blueground
Boston, MA, United States
S$ 264+
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Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield! - East Brookfield - Kitchen
Waterfront Retreat: 2BR with Huge Deck on Lake Lashaway Views in E. Brookfield!
East Brookfield, MA, United States
Free Wi-Fi
S$ 602+
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Luxury treat Tuscany style villa just few miles from downtown Boston - Newton - Living room
Luxury treat Tuscany style villa just few miles from downtown Boston
Newton, MA, United States
Free Wi-Fi
S$ 3,917+
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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
S$ 973+
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Luxury large house minutes to Cambridge and Boston - Watertown - Dining room
Luxury large house minutes to Cambridge and Boston
Watertown, MA, United States
Free Wi-Fi
S$ 1,409+
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Walk to Monument Beach Cape Cod Cottage with Grill - Bourne - Living room
Walk to Monument Beach Cape Cod Cottage with Grill
Bourne, MA, United States
9.6Wonderful(11)
Free Wi-Fi
S$ 445+
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Private Auburndale Getaway Minutes from Boston! - Newton - Living room
Private Auburndale Getaway Minutes from Boston!
Newton, MA, United States
Free Wi-Fi
S$ 481+
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Entire apartment with private entrance. - Chestnut Hill - Living room
Entire apartment with private entrance.
Chestnut Hill, MA, United States
Pet-friendly
S$ 495+
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Luxury Harvard/Mit Victorian - Cambridge
Luxury Harvard/Mit Victorian
West Cambridge
9.4Wonderful(34)
Parking
Free Wi-Fi
S$ 564+
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Charming Belmont Condo Near Boston condo - Belmont
Charming Belmont Condo Near Boston condo
Belmont, MA, United States
S$ 524+
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A Village Bed and Breakfast - Newton
A Village Bed and Breakfast
Newton, MA, United States
9.6Wonderful(88)
Parking
Free Wi-Fi
S$ 242+
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S$ 0 - S$ 837S$ 837 - S$ 1,673S$ 1,673 - S$ 2,509S$ 2,509 - S$ 3,345S$ 3,345+ per night

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Good to know

Low season

January

High season

December

Average price (weeknight)

S$ 407

Average price (weekend night)

S$ 353
Cheapest month to stay with an average 14% drop in price.
Most expensive month to stay with an average 55% 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

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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 Cambridge (50% of total searches to Massachusetts). The next most popular destination is Boston (50%).

  • 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 S$ 90. 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, houseboats, cabins, cottages, boats, chalets, farm stays, villas, agritourism, barns, campsites, bungalows, caravan parks and campgrounds.

  • What are some of the most-loved holiday rentals available in Massachusetts?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is 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 15% 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 holiday home.

What Massachusetts holiday rental guests are talking about

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Holiday rentals by topic

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Quarters On Dot By Thatch - Boston
Quarters On Dot By Thatch
South Boston
6.9Okay(818)
Free Wi-Fi
S$ 234+
Check availability
Boston Christopher - Boston
Boston Christopher
South End
7.8Good(375)
Free Wi-Fi
S$ 703+
Check availability

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Everything you need to know for your stay in Massachusetts

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