We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Massachusetts, United States

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
All Massachusetts Rentals
loading...
Sort by
Showing 1,000 of the 4,680 holiday rentals in Massachusetts.
For better results, choose a specific location.
From
$148
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 5
Water Views, Washer/Dryer, Pet friendly & more
11 photos Details
Reviews (3) Make Enquiry
From
$954
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Air Conditioning, Other outdoor space & more
14 photos Details
Reviews (3) Make Enquiry
From
$1,590
Per Week
1 Bedroom, 1 Bathroom, Sleeps 4
Parking, Suitable for children, Waterfront & more
13 photos Details
Reviews (1) Make Enquiry
From
$981
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Internet
13 photos Details
Reviews (1) Make Enquiry
From
$1,166
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
Other outdoor space, Grill
8 photos Details
Reviews (2) Make Enquiry
From
$1,267
Per Week
3 Bedrooms, 1 Bathroom, Sleeps 6
Internet, Other outdoor space, Air Conditioning & more
11 photos Details
Reviews (2) Make Enquiry
From
$154
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 2
Garden, Air Conditioning, Housekeeping Optional & more
14 photos Details
Reviews (3) Make Enquiry
From
$795
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Suitable for children, Other outdoor space & more
24 photos Details
Reviews (1) Make Enquiry
From
$1,007
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Parking, Washer/Dryer, Grill & more
9 photos Details
Reviews (1) Make Enquiry
From
$239
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 14
Fireplace, Washer/Dryer, Suitable for children & more
26 photos Details
Reviews (1) Make Enquiry
Get the List
From
$636
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 5
Grill, Other outdoor space
8 photos Details
Reviews (1) Make Enquiry
From
$2,438
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
Internet, Public pool, Grill & more
10 photos Details
Reviews (1) Make Enquiry
From
$3,127
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 8
Air Conditioning, Grill, Parking & more
13 photos Details
Reviews (2) Make Enquiry
From
$154
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Other outdoor space, Washer/Dryer, Parking & more
23 photos Details
Reviews (1) Make Enquiry
From
$1,325
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Washer/Dryer, Other outdoor space & more
10 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Grill, Suitable for children, Mountain Views & more
22 photos Details
Reviews (1) Make Enquiry
From
$1,590
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Other outdoor space, Internet, Washer/Dryer & more
11 photos Details
Reviews (1) Make Enquiry
From
$191
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Washer/Dryer, Game Room, Grill & more
23 photos Details
Reviews (3) Make Enquiry
From
$1,272
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 6
Washer/Dryer, Internet, Fireplace & more
10 photos Details
Reviews (2) Make Enquiry
From
$196
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Internet, Water Views, Grill & more
8 photos Details
Reviews (3) Make Enquiry
From
$1,060
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 4
Internet, Parking, Washer/Dryer & more
11 photos Details
Reviews (1) Make Enquiry
From
$106
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Internet, Other outdoor space, Shared Tennis Court & more
19 photos Details
Reviews (2) Make Enquiry
From
$848
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Public pool, Internet, Other outdoor space & more
16 photos Details
Reviews (1) Make Enquiry
From
$1,908
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space
10 photos Details
Reviews (1) Make Enquiry
From
$212
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
Elder access, Washer/Dryer, Air Conditioning & more
18 photos Details
Reviews (16) Make Enquiry
From
$6,891
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Internet, Air Conditioning, Grill
27 photos Details
Reviews (1) Make Enquiry
From
$3,604
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
Internet, Air Conditioning
15 photos Details
Reviews (1) Make Enquiry
From
$1,590
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
Grill, Washer/Dryer, Internet & more
20 photos Details
Reviews (3) Make Enquiry
From
$10,071
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 10
Internet, Air Conditioning, Pet friendly & more
16 photos Details
Reviews (1) Make Enquiry
From
$1,908
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
Grill, Air Conditioning, Internet
12 photos Details
Reviews (1) Make Enquiry
From
$1,908
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 5
Waterfront, Parking, Other outdoor space & more
13 photos Details
Reviews (1) Make Enquiry
From
$1,166
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
Internet, Other outdoor space
12 photos Details
Reviews (1) Make Enquiry
From
$2,120
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 9
Washer/Dryer, Internet, Other outdoor space & more
8 photos Details
Reviews (5) Make Enquiry
From
$848
Per Week
3 Bedrooms, 1 Bathroom, Sleeps 6
Other outdoor space, Washer/Dryer, Internet & more
14 photos Details
Reviews (1) Make Enquiry
From
$1,908
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Grill, Parking & more
15 photos Details
Reviews (2) Make Enquiry
From
$1,431
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 4
Public pool, Grill, Washer/Dryer & more
8 photos Details
Reviews (1) Make Enquiry
From
$4,240
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Internet, Air Conditioning, Parking & more
14 photos Details
Reviews (1) Make Enquiry
From
$1,325
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 8
Parking, Internet, Grill & more
17 photos Details
Reviews (1) Make Enquiry
From
$272
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Child pool, Air Conditioning, Washer/Dryer & more
9 photos Details
Reviews (1) Make Enquiry
From
$366
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children
14 photos Details
Reviews (4) Make Enquiry
From
$2,624
Per Week
5 Bedrooms, 8 Bathrooms, Sleeps 10
Other outdoor space, Parking, Grill & more
16 photos Details
Reviews (2) Make Enquiry
From
$106
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
Air Conditioning, Internet, Other outdoor space & more
13 photos Details
Reviews (4) Make Enquiry
From
$1,060
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Internet, Grill & more
11 photos Details
Reviews (2) Make Enquiry
From
$119
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Grill, Internet, Air Conditioning & more
14 photos Details
Reviews (4) Make Enquiry
From
$106
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Washer/Dryer, Mountain Views, Other outdoor space & more
9 photos Details
Reviews (3) Make Enquiry
From
$265
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Elder access, Grill, Housekeeping Optional & more
10 photos Details
Reviews (2) Make Enquiry
From
$530
Per Night
7 Bedrooms, 3 Bathrooms, Sleeps 14
Internet, Washer/Dryer, Parking & more
11 photos Details
Reviews (9) Make Enquiry
From
$226
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Fireplace, Internet & more
14 photos Details
Reviews (5) Make Enquiry
From
$2,438
Per Week
4 Bedrooms, 2 Bathrooms, Sleeps 10
Other outdoor space, Internet, Pet friendly
14 photos Details
Reviews (2) Make Enquiry
From
$1,696
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Air Conditioning, Washer/Dryer & more
14 photos Details
Reviews (1) Make Enquiry
Go to map view
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Massachusetts Vacation Rentals

Summer vacation rentals in Massachusetts are concentrated on Cape Cod. But despite the small area, you’ll find a huge variety of Cape Cod rental homes. Families might want a sprawling, cedar-shingled beach house in Chatham. College kids might opt to share a rental house within walking distance of Hyannis nightlife and bars. Or you could choose a romantic condo in Wellfleet. Our unbiased traveler reviews of Massachusetts vacation rental properties will help you plan your dream Cape Cod vacation. Let’s take a minute to cover the major regions of Cape Cod—once you know where you want to be, we can help you uncover a great deal on a Massachusetts vacation rental.

Massachusetts Beach Houses on the Upper Cape

Just so you know, the Upper Cape is the part of Cape Cod closest to the mainland. Beach houses in Bourne, vacation rentals in Falmouth, cottages in Mashpee and homes in Sandwich are all considered Upper Cape properties. (Yes, we know it’s weird that “Upper” and “Lower” have nothing to do with north and south. What can we say? Cape Cod is quirky.) If you rent a beach house here, you’ll have easier access to Boston and Plymouth (including Plimouth Plantation).

Mid-Cape Vacation Rentals

The Mid Cape is a popular location for Massachusetts beach houses. Hyannis is the biggest town here (it’s hardly urban, but it has an airport and a mall). Many Cape Cod fishing charters and boat tours leave from the docks in Hyannis (bring your camera—your captain might point out the Kennedy compound). Rent a historic home in Osterville for a small-town feel, or try a summer rental in Centerville to be close to sandy Craigville Beach.

Lower Cape Beach Cottages

The Lower Cape stretches from Harwich to Provincetown, encompassing the Cape Cod National Seashore, one of the most beautiful beaches in the U.S. Provincetown has enough antique stores, art galleries and boutiques to make it a fun destination even in the off-season, and it’s known as a gay- and lesbian-friendly town. Also, you’ll find some of Cape Cod’s best restaurants here. (When in doubt, go for the catch of the day.)

Cape Cod Activities

Your vacation rental in Massachusetts will put you close to terrific Cape Cod beaches, but there are plenty of other attractions and family-friendly activities to enjoy during your Cape Cod vacation. If you’re traveling to the Cape with kids, look into whale-watching cruises. Mini-golf is a great bet in the evenings, or make a sport of finding the best ice cream on Cape Cod. Outdoor activities on Cape Cod include biking on the Shining Sea Bike Trail or the Cape Cod Rail Trail—ask your landlord if your Massachusetts vacation rental property includes use of bikes!