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Villa vacation rentals in Massachusetts

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Top-rated villa rentals in Massachusetts

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Villa in Mashpee

4.8 out of 5 average rating, 50 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 Jacuzzi room! The house also boasts two living rooms, an extra private sleeping bedroom with two queen beds, central air, and an outdoor shower

Villa in Bourne

4.9 out of 5 average rating, 10 reviews

Cape Cod Gates

Welcome! Experience the charm of Cape Cod at our newly renovated retreat, 183 Sandwich Road, "Cape Cod Gates" This luxurious home offers 6 beds in 4 bedrooms, 2 baths, and ample space to relax. Located near the Bourne Bridge, it's perfect for exploring Boston or Cape. Enjoy our 38,000 sqft yard with a gazebo, heated pool, and parking for 3+ cars. Nearby, explore the Cape Cod Canal's trails, Scusset Beach, Old Silver Beach, Heritage Museum & Gardens. Book today and make unforgettable memories!

Villa in Chilmark

4.93 out of 5 average rating, 15 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.

Villa in Newton

4.93 out of 5 average rating, 55 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.

Villa in Cambridge

5 out of 5 average rating, 225 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

Villa in Manchester-by-the-Sea

4.98 out of 5 average rating, 52 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

Villa in Mashpee

5 out of 5 average rating, 39 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.

Villa in Charlton

4.77 out of 5 average rating, 65 reviews

Fall Villa near TreeHouse Brewery with 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.

Villa in Pittsfield

4.92 out of 5 average rating, 37 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).

Villa in Cape Cod

4.97 out of 5 average rating, 111 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

Villa in Barnstable

4.87 out of 5 average rating, 145 reviews

Spacious Lake House w Stunning Scenery

Huge, unique, private, Cape Cod vacation home in Cotuit. Beautiful lake villa with stunning views of lake and scenic views. Great for entertaining inside and outside the house. Grill overlooking the lake and huge private backyard. Beach pass provided for beast cape ocean beaches that are only minutes away. Restaurants, ice cream, movie theater, bowling and boutique stores minutes away. Great getaway vacation spot. Close to Osterville, Centerville, Mashpee, Falmouth, and Hyannis

Villa in Plymouth

5 out of 5 average rating, 33 reviews

Ocean View Luxury Villa with Inground Pool

Welcome to Villa on the Bluff. This beautiful contemporary villa has been designed for your comfort and viewing pleasure with architecture that intentionally focuses on the sweeping ocean view and the Italian mid-century interior which offers a deliciously enjoyable retreat. Step outside into a garden paradise enjoying the sounds of the frogs in the koi pond while sipping hot cocoa by the fire pit. Slip into our heated deep pool for endless fun with the family.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Bungalows

Intimate homes. inviting architecture

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Massachusetts villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Villa in Stockbridge

4.92 out of 5 average rating, 36 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

Villa in Newton

4.66 out of 5 average rating, 44 reviews

Beautiful Fall Stays

Villa in Cambridge

5 out of 5 average rating, 225 reviews

Phil's Harvard & MIT Home

Villa in Charlton

4.77 out of 5 average rating, 65 reviews

Fall Villa near TreeHouse Brewery with King Beds

Villa in Longmeadow

5 out of 5 average rating, 47 reviews

Comfort and Luxury - 180 year Old Gothic Estate

Villa in Nantucket

5 out of 5 average rating, 7 reviews

Center located, spacious villa 1 mile to town

Villa in Plymouth

5 out of 5 average rating, 33 reviews

Ocean View Luxury Villa with Inground Pool

Villa in Manchester-by-the-Sea

4.98 out of 5 average rating, 52 reviews

Secluded 20 Acre 10BR ultra contemporary Retreat

Luxury villa rentals

Villa in Gloucester

Salt Island Views: Walking distance to both Good

Villa in Mashpee

5 out of 5 average rating, 19 reviews

Beautiful home in New Seabury Close to beach-

Villa in Rockport

4.67 out of 5 average rating, 3 reviews

Pleasant House in Rockport: Old-world charm and

Villa in Wareham

4.21 out of 5 average rating, 14 reviews

Sprawling Beachfront Estate

Villa in Gloucester

4.6 out of 5 average rating, 5 reviews

Sunset Cove: Waterfront home in the Goose Cove

Villa in Gloucester

Over By Good Harbor: Phenomenal views and just

Villa in Plymouth

4.82 out of 5 average rating, 34 reviews

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

Villa in Somerset

5 out of 5 average rating, 6 reviews

House Private Access to Water

Villa rentals with a pool

Villa in Stockbridge

4.92 out of 5 average rating, 36 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

Villa in South Lee

4.79 out of 5 average rating, 122 reviews

Villa with Access to Amazing Amenities!

Villa in South Lee

4.68 out of 5 average rating, 34 reviews

Villa with Access to Various Amenities

Villa in Yarmouth

4.8 out of 5 average rating, 5 reviews

Cape Cod Villa steps away from beach/pool

Villa in Charlton

4.77 out of 5 average rating, 65 reviews

Fall Villa near TreeHouse Brewery with King Beds

Villa in Longmeadow

5 out of 5 average rating, 47 reviews

Comfort and Luxury - 180 year Old Gothic Estate

Villa in Newton

4.93 out of 5 average rating, 55 reviews

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

Villa in Plymouth

5 out of 5 average rating, 33 reviews

Ocean View Luxury Villa with Inground Pool

Destinations to explore