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Villa vacation 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.

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Villa in Chilmark

5.0 out of 5 average rating, 11 reviews

3 Bedroom house w Guest Cottage off of Middle Road

Well located off beloved Middle Road, property embodies all of the natural beauty of Chilmark: old stone walls, perennial plantings & mature trees. Property abuts 100 acres of Sheriff's Meadow Conservation land. Main house has three bedrooms w ensuite baths. A separate guest cottage w a bedroom, full bath, covered porch, kitchenette & back deck w outdoor shower. Main and guest house have air conditioning. Guest house & little summer bunkhouse meant for summer use. Oct-May max 6 people.

Nov. 5 – 12

$1,693 CAD per night

Guest favourite

Villa in Newton

4.91 out of 5 average rating, 45 reviews

Explore Boston in style! Dream home, pool, sauna.

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - one of the most desirable and safe suburbs of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

Nov. 13 – 20

$1,108 CAD per night

Guest favourite

Villa in Cambridge

4.99 out of 5 average rating, 188 reviews

Phil's Harvard & MIT Home

* An entire apartment with a Harvard bedroom and an MIT bedroom Right at the heart of Harvard University, we are seconds away from university facilities and key attractions, making it a perfect place to stay if you are interested in exploring Harvard. The house is in traditional Victorian style with a lot of history while the interior was renovated in 2016. There are two bedrooms of unique styles: The Harvard and MIT rooms. * Please view my other listings for renting one of the bedrooms only

Aug. 21 – 28

$556 CAD per night

Guest favourite

Villa in Mashpee

5.0 out of 5 average rating, 33 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days, power outage won't be an issue if you can steal away to this home, with an indoor heated salt water pool and hot tub fully equipped with a backup generator, with a view of the famous 13-Hole Championship Golf Course Cape Cod. Our ultimate luxury home is filled with arcades, air hockey, foosball and other indoor entertainments for guests to enjoy, comfortably sleeps 6-8 and just a few minute drive to all of the amenities New Seabury has to offer.

Oct. 31 – Nov. 7

$1,733 CAD per night

Guest favourite

Villa in Manchester-by-the-Sea

4.97 out of 5 average rating, 37 reviews

Secluded 20 Acre 10BR ultra contemporary Retreat

Family gatherings and family reunions. Make those family memories at this ultra contemporary take on a tree house. Original design based off the iconic Farnsworth house, updated with 10 Bed rooms of individual climate control atop of 20 acres of wildlife. Designer kitchen for the professional chef. Privacy that most movie stars long for. 5 min to beaches 10 min to Gloucester 20 min to historic Salem 45 min to Boston. Pesticide free landscaping Great location for family gatherings and reunions

Dec. 18 – 25

$1,517 CAD per night

Guest favourite

Villa in Pittsfield

4.93 out of 5 average rating, 30 reviews

Luxurious Berkshire Mountain Retreat!!

Escape to the Berkshires at this 2 acre, private retreat. Gleaming hardwood floors, handmade Amish furniture, large interior and exterior areas for family activities as well as a heated in-ground pool with a slide for the kids that is open during the summer months! Given the 4 bedrooms and additional sleeping areas, this spacious ranch is suited for up to 6-8 guests with the ability to host more (there is a 1 bedroom pool house that can sleep an additional 2 guests for an additional charge).

Jul. 14 – 21

$1,287 CAD per night

Villa in Charlton

4.75 out of 5 average rating, 55 reviews

Summer Villa: Private Pool, Playground, King Beds

Bring the whole family to this lovely villa with lots of free parking and multiple comfy King Beds. This Villa seats on 1 Acre in a really residential and quiet neighborhood in Charlton MA. The property boasts of a spacious backyard with a private play ground for kids and a private pool with a large deck. It's less than 10 minutes away from the Treehouse brewery. The Heritage Country Club golf course is about 10 minutes from the Villa. There are several lakes within 20 minutes from the Villa.

Oct. 4 – 11

$680 CAD per night

Villa in Gloucester

4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo. This home has a custom kitchen, spacious open concept living/dining room and lots of windows. There are two master bedroom suites with full baths on two separate floors as well as a sleeper sofa in the living room. There are water views from just about every window. Multiple

Jun. 5 – 12

$916 CAD per night

Villa in Mashpee

4.8 out of 5 average rating, 41 reviews

Expansive Beach House - Outdoor Jacuzzi, Shower…

Outdoor JACUZZI, SHOWER, Come stay at our expansive beach house located steps from Popponeset Bay and down the road from multiple beaches, Mashpee Commons, golf courses, hiking trails, restaurants, Children's Museum, and more! Long day at the beach? Relax at the house on the back deck, enjoy the large back yard, or hop in the brand new enclosed private 8 person Jacuzzi. The house also boasts two living rooms, an extra sleeping room with two queen beds, central air, and an outdoor shower.

Sep. 23 – 30

$1,137 CAD per night

Villa in Plymouth

4.86 out of 5 average rating, 29 reviews

Oceanfront Villa, AC, TV, Free WiFi, Pet Friendly

Fabulous oceanfront house with a public beach in 8 minute by walk. You can also access to its own private beach if you are nimble. 2.5 Miles to Plymouth historic town center and waterfront docked Mayflower Ship. The Plymoth Plantation is around the corner. Easy to get to Cape Cod and Boston. The villa has everything a family would need to enjoy a great vacation. Prefer week long rentals, check in/out on Saturday. Shorter term in off season. Contact us for special periods and quotes.

Apr. 13 – 20

$1,814 CAD per night

Guest favourite

Villa in Newbury

4.91 out of 5 average rating, 65 reviews

Coastal Modern Beachfront Chalet, sleeps 10+

Beachfront family fun in a modern, stylish villa that's been completely renovated with upscale amenities. Watch the waves crash as you enjoy winding down on the deck or going for a walk to the jetty. Bars, restaurants, ice cream shops, convenience stores all within walking distance of the front door. This ultra comfy beach house is also mins away from amazing downtown Newburyport with shops and top notch restaurants galore! Bunk room is on the first floor as you walk into the house.

Dec. 9 – 16

$1,072 CAD per night

Guest favourite

Villa in Cape Cod

4.98 out of 5 average rating, 99 reviews

Cape Cod Villa * Vacation * Spa * Retreat * Venue

Pond Front Villa in the Woods. A year-round destination for family trips, small gatherings, bird watchers, yoga, bicycling enthusiasts & work trips. Located in the heart of the picturesque Lower Cape, encompasses the historic towns of Orleans, Chatham, Harwich, and Brewster. We provide resort-class on site group activities. Located on Grassy Pond, close to shopping, Long Pond, Pleasant Bay and Nauset Beach. Few minutes to the highway. No places or activities within walking distance

Sep. 6 – 13

$1,594 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Bungalows

Intimate homes, inviting architecture

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Massachusetts villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Villa in Barnstable

4.75 out of 5 average rating, 93 reviews

Walk to beaches & ferries ★ Snow's Creek Waterview

Nov. 30 – Dec. 7

$807 CAD per night

Villa in Gloucester

4.67 out of 5 average rating, 3 reviews

Helena House: European flair, close to Plum Cove

Nov. 30 – Dec. 7

$665 CAD per night

Guest favourite

Villa in Cambridge

4.99 out of 5 average rating, 188 reviews

Phil's Harvard & MIT Home

Aug. 21 – 28

$556 CAD per night

Villa in Barnstable

4.87 out of 5 average rating, 135 reviews

Spacious Lake House w Stunning Scenery

Apr. 25 – May 2

$1,117 CAD per night

Guest favourite

Villa in Mashpee

5.0 out of 5 average rating, 33 reviews

Heated Indoor Pool & Spa - Golf Course View

Oct. 31 – Nov. 7

$1,733 CAD per night

Guest favourite

Villa in Newbury

4.91 out of 5 average rating, 65 reviews

Coastal Modern Beachfront Chalet, sleeps 10+

Dec. 9 – 16

$1,072 CAD per night

Guest favourite

Villa in Longmeadow

5.0 out of 5 average rating, 37 reviews

Comfort and Luxury - 180 year Old Gothic Estate

Feb. 2 – 9

$1,323 CAD per night

Guest favourite

Villa in Manchester-by-the-Sea

4.97 out of 5 average rating, 37 reviews

Secluded 20 Acre 10BR ultra contemporary Retreat

Dec. 18 – 25

$1,517 CAD per night

Luxury villa rentals

Villa in Stockbridge

4.84 out of 5 average rating, 45 reviews

The Taggart House

Jan. 10 – 17

$1,716 CAD per night

Villa in Mashpee

5.0 out of 5 average rating, 18 reviews

Beautiful home in New Seabury Close to beach-

Jun. 2 – 9

$1,323 CAD per night

Guest favourite

Villa in Somerset

5.0 out of 5 average rating, 6 reviews

House Private Access to Water

Mar. 8 – 15

$1,093 CAD per night

Villa in Nantucket

5.0 out of 5 average rating, 4 reviews

Center located, spacious villa 1 mile to town

Jan. 9 – 16

$937 CAD per night

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

Sep. 5 – 12

$1,522 CAD per night

Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

Jan. 3 – 10

$1,070 CAD per night

Villa in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck

Villa in Gloucester

Salt Island Views: Walking distance to both Good

Dec. 25 – Jan. 1

$1,077 CAD per night

Villa rentals with a pool

Guest favourite

Villa in Cambridge

4.99 out of 5 average rating, 188 reviews

Phil's Harvard & MIT Home

Aug. 21 – 28

$556 CAD per night

Villa in South Lee

4.69 out of 5 average rating, 32 reviews

Villa with Access to Various Amenities

Jun. 19 – 26

$393 CAD per night

Guest favourite

Villa in Pittsfield

4.93 out of 5 average rating, 30 reviews

Luxurious Berkshire Mountain Retreat!!

Jul. 14 – 21

$1,287 CAD per night

Guest favourite

Villa in South Lee

4.81 out of 5 average rating, 21 reviews

Spacious Villa with Access to Various Amenities!

May 18 – 25

$452 CAD per night

Guest favourite

Villa in Stockbridge

4.91 out of 5 average rating, 32 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

Jan. 4 – 11

$869 CAD per night

Guest favourite

Villa in Longmeadow

5.0 out of 5 average rating, 37 reviews

Comfort and Luxury - 180 year Old Gothic Estate

Feb. 2 – 9

$1,323 CAD per night

Guest favourite

Villa in Newton

4.91 out of 5 average rating, 45 reviews

Explore Boston in style! Dream home, pool, sauna.

Nov. 13 – 20

$1,108 CAD per night

Guest favourite

Villa in Mashpee

5.0 out of 5 average rating, 33 reviews

Heated Indoor Pool & Spa - Golf Course View

Oct. 31 – Nov. 7

$1,733 CAD per night

Destinations to explore