Villa holiday rentals in Massachusetts
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Top-rated villa rentals in Massachusetts
Guests agree: These villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts villa rentals
Private villa rentals
Villa in Gloucester
4.67 out of 5 average rating, 3 reviewsHelena House: European flair, close to Plum Cove
21–28 Sep
Villa in Cambridge
4.99 out of 5 average rating, 188 reviewsPhil's Harvard & MIT Home
8–15 Oct
Villa in Barnstable
4.87 out of 5 average rating, 135 reviewsSpacious Lake House w Stunning Scenery
15–22 Jan
Villa in Mashpee
5.0 out of 5 average rating, 33 reviewsHeated Indoor Pool & Spa - Golf Course View
31 Oct – 7 Nov
Villa in Longmeadow
5.0 out of 5 average rating, 37 reviewsComfort and Luxury - 180 year Old Gothic Estate
2–9 Feb
Villa in Pittsfield
4.93 out of 5 average rating, 30 reviewsLuxurious Berkshire Mountain Retreat!!
15–22 Oct
Villa in Chilmark
5.0 out of 5 average rating, 11 reviews3 Bedroom house w Guest Cottage off of Middle Road
5–12 Nov
Villa in Cape Cod
4.98 out of 5 average rating, 99 reviewsCape Cod Villa * Vacation * Spa * Retreat * Venue
2–9 Apr
Luxury villa rentals
Villa in Stockbridge
4.84 out of 5 average rating, 45 reviewsThe Taggart House
9–16 Jan
Villa in Mashpee
5.0 out of 5 average rating, 18 reviewsBeautiful home in New Seabury Close to beach-
1–8 Jun
Villa in Somerset
5.0 out of 5 average rating, 6 reviewsHouse Private Access to Water
6–13 Sep
Villa in Nantucket
5.0 out of 5 average rating, 4 reviewsCenter located, spacious villa 1 mile to town
6–13 Nov
Villa in Rockport
4.67 out of 5 average rating, 3 reviewsPleasant House in Rockport: Old-world charm and
5–12 Sep
Villa in Gloucester
Over By Good Harbor: Phenomenal views and just
11–18 Nov
Villa in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck
Villa in Gloucester
Salt Island Views: Walking distance to both Good
8–15 Sep
Villa rentals with a pool
Villa in Cambridge
4.99 out of 5 average rating, 188 reviewsPhil's Harvard & MIT Home
8–15 Oct
Villa in South Lee
4.69 out of 5 average rating, 32 reviewsVilla with Access to Various Amenities
6–13 Jan
Villa in Pittsfield
4.93 out of 5 average rating, 30 reviewsLuxurious Berkshire Mountain Retreat!!
15–22 Oct
Villa in Longmeadow
5.0 out of 5 average rating, 37 reviewsComfort and Luxury - 180 year Old Gothic Estate
2–9 Feb
Villa in Mashpee
5.0 out of 5 average rating, 33 reviewsHeated Indoor Pool & Spa - Golf Course View
31 Oct – 7 Nov
Villa in South Lee
4.81 out of 5 average rating, 21 reviewsSpacious Villa with Access to Various Amenities!
23 Feb – 2 Mar
Villa in Plymouth
5.0 out of 5 average rating, 26 reviewsOcean View Luxury Villa with Inground Pool
10–17 Jun
Villa in Stockbridge
4.91 out of 5 average rating, 32 reviewsHistoric Stockbridge Villa on 25 acres sleeps 16
23–30 Jan
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