Luxury rentals in Massachusetts

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Top-rated luxury holiday rentals in Massachusetts

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Luxe

A spacious outdoor area features a swimming pool with a curved design, surrounded by a stone patio and lounge chairs. The house, characterized by a classic colonial style, has multiple sliding doors that open to the pool area, framed by well-kept greenery and a landscaped garden.

Villa in Nantucket

Eastbound

Ideal for a group or family vacation, this is an idyllic, spacious house replete with colonial flavor and set among Nantucket’s historic streets. Boasting a cheery fireplace, chandelier, and ample dining space, fresh Atlantic air flows over the tended, landscaped garden, complete with flower beds and pool. Numerous museums, sandy beaches, quaint streets and tempting eateries are a short walk away. Swaying trees and the dynamic sky of this famous island backdrop the clean, sloped outline of the house, with a pastoral, flagstone path leading to the cheery entrance. Stepping past the shaded porch seats (a favorite afternoon spot), pass through cool air conditioning as you take a seat amongst the pleasantly-lit, fashionable furniture. Tasteful tiling and classic, clear glass runs throughout the home’s numerous bathrooms, while the straight-forward comfort and simple themes of the bedrooms promise a fine night’s sleep. With a full complement of updated appliances, kitchen space and a lengthy dining table, imagine relaxed, laid-back dinners under the soft yellow glow of the overhead chandeliers. Eastbound’s proximity to the core of old Nantucket will add to the sheer convenience of any visit. Guests are just a short walk from quaint parks, stimulating art galleries, and established museums that delve into the island’s rich history, while a bracing swim or sunny afternoon awaits at nearby Steps Beach and Jetties Beach. Get a feel for the island’s geography with eye-opening cliff walks, or hit downtown for a satisfying evening meal, choosing from international choices or renowned seafood. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Private balcony • Bedroom 3: King size bed, Ensuite bathroom with with stand-alone shower, Television • Bedroom 4: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Walk-in closet Sunset Cottage • Bedroom 5: Twin size bunk bed, 2 Twin size beds, Ensuite bathroom with shower/bathtub combo FEATURES & AMENITIES • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

A well-lit living area is defined by wooden beams and large windows, allowing natural light to fill the space. A brown leather sofa and two armchairs face a circular coffee table. Decorative elements and a stone feature wall add character to the room.

Villa in Bourne

4.95 out of 5 average rating, 22 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!

Luxe

An aerial view showcases the expansive outdoor area of the property, featuring a large deck surrounding a rectangular pool. The sunset casts a warm glow over the landscape, which includes lush greenery and distant residential structures.

Home in Nantucket

Shangri-La Meets Nantucket

Welcome to The Big Dip, a seven-bedroom home with an additional studio above the garage. The interiors have been stylishly curated with a focus around modern sophistication, minimalism & clean lines. Made for retreat, The Big Dip offers a separate office, media room, full gym & sauna. With lavish Ipe decking, the outdoor oasis lets you lounge poolside, converse by the firepit & dine al fresco! Enjoy the full service cabana with drop-down movie screen, living area, half bath, kitchen & bar.

Luxe

A spacious two-story building is framed by a tranquil pool and a cozy fire pit. The warm glow of outdoor lanterns illuminates the exterior, while relaxing seating areas are arranged around the pool and along the side, inviting leisure and comfort.

Home in Nantucket

5 out of 5 average rating, 12 reviews

The Dunes

Indulge in luxury and comfort at The Dunes in Nantucket. With exquisite design, opulent interiors, and stunning outdoor spaces, The Dunes offers endless possibilities for unforgettable experiences. Enjoy gourmet meals, relax by the tranquil pool, or explore the outdoors. With unbeatable proximity to Nantucket's downtown and pristine beaches, The Dunes is perfect for an indulgent retreat. Immerse yourself in a sensory journey where every moment is a celebration of the finest things in life.

Luxe

The exterior of the home is showcased at dusk, with warm lighting emerging from the windows. Lounge chairs are positioned near a swimming pool, and a patio table with an umbrella is visible. Lush grass and stone pathways enhance the outdoor setting.

Villa in Nantucket

5 out of 5 average rating, 13 reviews

Three Cliff Lane

Discover the ultimate Nantucket retreat! Our 5-BR home with a separate 1-BR guest house is the perfect vacation rental in the coveted Cliff area. Relax by the pool in the spacious yard, or take a stroll to Steps Beach just moments away. With a prime location just 1 mile from downtown, you'll have easy access to shopping, dining, and entertainment. This beautifully appointed, Sophie Metz designed property offers the ideal blend of luxury and prime location for your island getaway.

Luxe

A spacious outdoor area features a newly constructed home with a welcoming porch and a detached garage. Neatly landscaped gardens surround the gravel driveway, while expansive lawns provide ample outdoor space. A clear blue sky enhances the home's appealing exterior, reflecting a serene environment.

Home in Edgartown

Beautiful New Katama Getaway!

Discover a spacious 4 bedroom, 4.5 bathroom retreat in Katama. This beautiful, new construction home offers a blend of comfort and luxury, perfect for relaxing or gathering with family and friends. Enjoy a gourmet kitchen, spacious bedrooms including 2 primary suites, and ample outdoor space. Close proximity to the beach, bike paths, and Edgartown ensures easy access to all Martha's Vineyard has to offer. Experience coastal living at its finest in this stunning island getaway!

Luxe

A modern home with a curving roof features floor-to-ceiling windows that reflect the soft colors of sunset. The exterior combines stone and wood elements, surrounded by lush greenery. A pathway leads to the main entrance, integrating outdoor and indoor spaces.

Home in New Marlborough

5 out of 5 average rating, 3 reviews

Sunset Falls: A Berkshire Mountain Luxury Retreat

Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. Open-concept living areas, floor-to-ceiling windows, and spacious great room. Breathtaking mountain views and full-service luxury amenities. Perfect for family gatherings and romantic getaways, this private oasis provides a serene escape, promising a unique, pampered experience with concierge service, ensuring a stay beyond the typical Airbnb.

Luxe

The stately mansion features multiple outdoor seating areas, including comfortable lounge chairs arranged on a stone patio. The venue's iconic architecture is visible in the background, framed by well-maintained greenery and a bright blue sky.

Place to stay in Lenox

The Kemble Berkshires

Located in Lenox, one of Berkshire's most vibrant towns, this Gilded Age mansion is a beautiful event space with sweeping mountain views from the heart of the town. Your large group will appreciate the estate’s generous outdoor entertaining area, games rooms, and chef’s kitchen. In town, you’ll find delightful restaurants, bakeries, and antique shops. Copyright © Luxury Retreats. All rights reserved.

Luxe

The exterior of the vacation rental showcases a two-story house surrounded by lush greenery and colorful foliage. A spacious porch with seating faces the ocean, which is visible in the distance. Clear blue skies enhance the inviting atmosphere of the property.

Home in Nantucket

5 out of 5 average rating, 9 reviews

4 bed 3.5 bath, heated pool & spa, ocean views

This 2020 renovated and beautifully appointed Nantucket vacation rental has a heated pool, spa, and distant views of the ocean and pastoral views looking towards Sconset and Sankaty Head Lighthouse. The perfect spot for a relaxing vacation. To see a video of the property, please search "3 Parson Lane Nantucket" on YouTube

Luxe

A spacious living area is highlighted by a large fireplace and a sleek television mounted above it. Comfortable seating arranged around a central coffee table invites relaxation. A leafy plant adds a touch of greenery, while natural light fills the space through nearby windows.

Home in Yarmouth

5 out of 5 average rating, 11 reviews

Cape Cod Family Vacation

This New Luxurious property for your vacation on Cape Cod , the house sleeping arrangements for 13-It's an Excellent choice for a family and a group of friends . Welcoming home has everything you'll need for a comfortable stay and relaxing vacation . Bring your family to enjoy the summer on Cape .

Luxe