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
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Popular amenities for villa rentals in Massachusetts
Private villa rentals
Villa in Barnstable
4.75 out of 5 average rating, 93 reviewsWalk to beaches & ferries ★ Snow's Creek Waterview
10–17 Dec
Villa in Gloucester
4.67 out of 5 average rating, 3 reviewsHelena House: European flair, close to Plum Cove
28 Nov – 5 Dec
Villa in Cambridge
4.99 out of 5 average rating, 187 reviewsPhil's Harvard & MIT Home
18–25 Aug
Villa in Barnstable
4.87 out of 5 average rating, 135 reviewsSpacious Lake House w Stunning Scenery
24–31 Dec
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, 36 reviewsComfort and Luxury - 180 year Old Gothic Estate
8–15 Apr
Villa in Manchester-by-the-Sea
4.97 out of 5 average rating, 37 reviewsSecluded 20 Acre 10BR ultra contemporary Retreat
27 Feb – 6 Mar
Villa in Pittsfield
4.93 out of 5 average rating, 30 reviewsLuxurious Berkshire Mountain Retreat!!
15–22 Oct
Luxury villa rentals
Villa in Stockbridge
4.84 out of 5 average rating, 45 reviewsThe Taggart House
17–24 Mar
Villa in Mashpee
5.0 out of 5 average rating, 18 reviewsBeautiful home in New Seabury Close to beach-
31 May – 7 Jun
Villa in Somerset
5.0 out of 5 average rating, 6 reviewsHouse Private Access to Water
6–13 Sept
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 Sept
Villa in Gloucester
Over By Good Harbor: Phenomenal views and just
16–23 Jun
Villa in Gloucester
Perrywinkle: Waterfront on Gloucester’s Rocky Neck
Villa in Gloucester
Salt Island Views: Walking distance to both Good
8–15 Sept
Villa rentals with a pool
Villa in Cambridge
4.99 out of 5 average rating, 187 reviewsPhil's Harvard & MIT Home
18–25 Aug
Villa in South Lee
4.69 out of 5 average rating, 32 reviewsVilla with Access to Various Amenities
29 Oct – 5 Nov
Villa in Pittsfield
4.93 out of 5 average rating, 30 reviewsLuxurious Berkshire Mountain Retreat!!
15–22 Oct
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, 36 reviewsComfort and Luxury - 180 year Old Gothic Estate
8–15 Apr
Villa in South Lee
4.81 out of 5 average rating, 21 reviewsSpacious Villa with Access to Various Amenities!
24 Feb – 3 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
4.9 out of 5 average rating, 31 reviewsHistoric Stockbridge Villa on 25 acres sleeps 16
22–29 Jan
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