Villa holiday rentals in Massachusetts

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Top-rated villa rentals in Massachusetts

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Top Guest favourite
A wooden bed frame with a patterned quilt is featured in the center of a softly lit bedroom. Floral-patterned curtains adorn the windows, and a bedside lamp provides additional light. A decorative rug is positioned on the hardwood floor, adding warmth to the space.
Private room in Boston
4.96 out of 5 average rating, 51 reviews

Charming & Cozy Bedroom for Single or Couple

Welcome to our century-old home. Just a 5-minute walk away is Reservation Park for morning exercises or relaxation. Our serene neighborhood boasts tall evergreen trees. Our historic house was featured in the movie Spotlight, earning recognition with the 2016 Academy Award. Convenience is key with nearby bus routes (35, 36, 37, 38, 34, 34E, 40) to the Orange Line subway. Major amenities are a 15-minute walk away. Parking is available. Boston College is a 15-minute drive away. Warmly welcome!

Top Guest favourite
The contemporary tree house stands prominently against a clear blue sky, featuring expansive floor-to-ceiling windows that invite natural light. A vibrant blue staircase leads to the entrance. Lush greenery and carefully arranged landscaping enhance the modern design, creating a harmonious connection with nature.
Villa in Manchester-by-the-Sea
4.97 out of 5 average rating, 66 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

Top Guest favourite
A wooden dining table with two chairs is positioned along the riverside, offering views of the water and distant landscapes. Two wine glasses and a bottle are placed on the table, set against a backdrop of soft sunset clouds reflecting on the river's surface.
Villa in Somerset
5 out of 5 average rating, 16 reviews

House Private Access to Water

Welcome to a Romantic & Memorable Place that doesn't just provide luxurious modern accommodation for families but also lets you relax by the Exquisite water view Paradise. Bedrooms where guests enjoy the breath-taking scenic waterfront are greeted by beautiful white swans, ducklings and crane in the morning. Quiet Bay where guests enjoy coffee out front with a spectacular view of the sunrise, and cocktails/bbq with beautiful sunset. 2 Bedrooms w/KingBed, 1 BR w/2 Full Beds, 1 BR w/2 twin beds

A modern kitchen is presented, featuring wooden cabinetry and a large granite island with seating for four. Stainless steel appliances are visible, including an oven and a refrigerator. Soft yellow lighting creates a warm ambiance, complementing the hardwood floors.
Villa in Charlton
4.64 out of 5 average rating, 78 reviews

Relaxing Fall Escape Home near TreeHouse Brewery

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.

Top Guest favourite
A scenic view of the Cape Cod Villa entrance showcases a staircase leading to the main entrance, framed by lush greenery and a vibrant maple tree. The gravel path winds gently, adding to the serene ambiance of the private conservation land.
Villa in Cape Cod
4.98 out of 5 average rating, 125 reviews

Cape Cod Villa retreat, spa, venue, film location

Cape Cod Villa, an award-winning sanctuary on 1.8 acres of private conservation land, embodies refined luxury and serenity. Designed by Domapine Decor, this exclusive estate offers stunning interiors and panoramic pond views, placing guests moments from Cape Cod’s finest beaches, elite golf courses, and acclaimed dining. A haven of tailored indulgence, the villa offers private spa treatments and chef-curated dining, delivering an unparalleled escape in Lower Cape’s most sought-after setting.

A clean and modern bathroom features a spacious soaking tub with sleek fixtures. Large windows allow natural light to illuminate the space, showcasing a view of lush greenery and blooming flowers. Fresh towels and potted plants add a touch of warmth to the serene setting.
Villa in Mashpee
5 out of 5 average rating, 19 reviews

Beautiful home in New Seabury Close to beach-

The house is located in an ultra private prestigious New Seabury resort on Cape Cod, a bike ride to Popponesset, The Spit beach and Market Place(less than a mile). Day trip to Martha's Vineyard and Nantucket island is a ferry away....The house has hardwood floors, cathedral, vaulted and beamed ceilings with skylights, 3 bedrooms and 2-5 baths and a large den/office....with a wrapped around deck of over 800sq ft overlooking almost an acre of private land filled with pine trees...

Guest favourite
A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.
Villa in Wareham
4.88 out of 5 average rating, 90 reviews

Perfect Farmhouse for groups-golf/trails/beach

Old Red Farm Inn invites you to forget your worries in this charming space that has everything to offer. Originally built in 1700’s, this updated Inn can be your sanctuary! A perfect fall getaway! A lagoon pool on site, a golf course across the street, walking distance to Little Harbor Beach, and acres of conservation land for hiking provides everything you need in order to relax. This home is over 5,000 ft. and can fit multiple families that are looking for a fun getaway.

A serene beach scene is framed by overhanging trees, showcasing a sandy shore meeting gentle waves. The horizon displays a calm ocean under a clear blue sky, with small boats visible in the distance. The rocky shoreline adds to the natural beauty of the setting.
Villa in Plymouth

New! Ocean Views & Private Beach 3br Nature Escape

Escape to this beautiful 3-bedroom home perfectly nestled in nature, offering breathtaking ocean views from every floor. Wake up to the soothing sounds of the waves and enjoy panoramic vistas that stretch across the horizon. Whether you’re sipping your morning coffee or unwinding at sunset, the scenery will captivate you at every turn. This spacious, light-filled home comfortably accommodates families or groups, with three cozy bedrooms designed for restful nights.

Superhost
The tranquil surface of Bulloughs Pond reflects the surrounding greenery and the warm hues of a well-maintained house in the background. Framed by lush leaves, the scene captures the natural beauty of the area, inviting moments of solitude by the water.
Villa in Newton
4.71 out of 5 average rating, 55 reviews

Lake side Villa - Newtonville

The pond is iced and the fireplace roaring! 5 bedrooms 2 with uninterrupted water views, full waterfall bath, Private master. Beamed and sunken living room, beehive fireplace, fire-pit, propane grill. Stainless kitchen w/ entertainer sized island overlooking pet friendly yard. Seating for 24 diners inside plus veranda. Our beautiful grounds will delight your family. Off street driveway for 3 vehicles. First, last security lease agreement long term stays please

Top Guest favourite
The villa's exterior showcases a large three-story structure, adorned with white siding and multiple windows. A spacious deck leads to the front entrance, framed by greenery from surrounding trees. The sky above is partly cloudy, providing a serene backdrop.
Villa in Stockbridge
4.95 out of 5 average rating, 58 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

Top Guest favourite
The kitchen features modern appliances, including a stainless steel refrigerator and stove. A white countertop extends into a pass-through bar, with a bowl of snacks displayed. Natural light filters through the window, illuminating the sleek cabinetry and grey tile backsplash.
Villa in Cambridge
4.98 out of 5 average rating, 290 reviews

Phil's Harvard & MIT Home

Located in the heart of Harvard University, this charming Victorian apartment offers a unique and memorable stay just steps from campus landmarks and local attractions. The home's classic architecture reflects its history, while the updated interior provides modern comfort. The uniquely styled Harvard and MIT bedrooms are inspired by the spirit of their namesake universities, perfect for visitors seeking an immersive Cambridge experience.

Superhost
An aerial view of the antique house surrounded by lush greenery, highlighting the spacious outdoor area. A well-maintained lawn is complemented by a fire pit seating arrangement and shaded by mature trees. The layout suggests easy access to nearby roads and ample parking space.
Villa in Barnstable
4.77 out of 5 average rating, 126 reviews

Walk to beaches & ferries ★ Snow's Creek Waterview

6BR/2.5BA - 0.5 miles from Veteran & Kalmus beach! Escape to our enchanting beachside retreat, stunning lake views, where history and comfort converge to create lasting memories. You will love the location of this antique Hyannis home! Tons of local attractions & amenities are minutes away including Veteran & Kalmus Beach, local shops, restaurants & boutiques along Main Street, all under a mile away! Hosting up to 14 people!

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