Luxury rentals in Massachusetts

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Top-rated luxury holiday rentals in Massachusetts

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Luxe

Home in Wellesley

Luxury Boston Mansion | Outdoor Gardens + Sauna

Meet our lovely 1800's victorian, thoughtfully renovated & fully restored luxury victorian with a custom kitchen/baths walk to shopping, restaurants, parks & train. The home features an incredible backyard w/ outdoors living, dining and fire pit area, farmers porch.! This incredible stay is only 20 min to downtown Boston! Need more space? ask about our au-pair suite space Dates not available? Looking to host a photo shoot? Message us! Check out our other bespoke stays at Elsewherewithme

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Luxe

Home in Chatham

4.88 out of 5 average rating, 56 reviews

Steps to Beach + Game Room + Porch | Coastal Haven

Welcome to Coastal Haven! — a spacious seaside escape perfect for families or groups. Steps from the beach, Main St & Chatham Bars Inn, this elegant 10-bed retreat blends comfort, fun, and Cape Cod charm. 📍 0.4 mi to beach, 0.5 mi to charming Main St & Chatham Bars Inn 🌅 Tranquil front porch & lawn with kids’ playset 🎱 Game room: pool table, Apple TV, games ✨ Open-concept living with stunning 2-story glass walls 🧺 Full kitchen, laundry, fast WiFi 🛏️ 10 beds + soundproof divider setup

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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

5.0 out of 5 average rating, 17 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.

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Luxe

Home in New Marlborough

5.0 out of 5 average rating, 4 reviews

Sunset Falls Estate, 167 Private Acres, Berkshires

A Berkshire private mountain estate in New Marlborough, MA 167 acres — home at 1,400 ft, summit at 1,640 Five ensuite bedrooms + the Bunk Room — sleeps 16 Indoor cedar spa room including cedar infrared sauna, cold plunge tub and steam room Expansive deck with hot tub, mountain views, lounging/dining Two wood-burning fireplaces, three fire pits, marked trails across the mountain Central to Great Barrington, Stockbridge, Litchfield County, Hudson Valley Concierge services available

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Luxe

A spacious living area is adorned with a neutral palette, featuring a plush sofa and stylish armchairs surrounding a glass coffee table. A round dining table with woven chairs occupies one corner, complemented by elegant lighting fixtures and soft drapes enhancing the ambiance.

Home in South End

5.0 out of 5 average rating, 6 reviews

*NEW* Ultra-Luxury 4bd Boston Designer Brownstone

**NEW** Experience one of Boston’s most exclusive private homes. Rarely available, this sunny 4BR/3.5BA luxury brownstone is in the South End/Back Bay. Set in a fully restored 1830s Victorian and designed by a top Boston designer, it features a chef’s kitchen, grand master suite, spa-like baths, designer furnishings, and a serene private patio. Walk the cobble stones of south end, Newbury st, Public Garden, and Copley Square. Only 3 min walk to Back Bay Station for easy train access.

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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

5.0 out of 5 average rating, 16 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.

HospitalityLocationAmenitiesWalkabilityConditionSleep qualityComfortIndoor spacesCleanlinessFamilyPoolBack gardenAccuracyBathroomKitchenCheckoutLayoutBikingCheck-in

Luxe

Home in Dedham

4.92 out of 5 average rating, 13 reviews

The Charles Château Private Estate

Unique and distinctively remodeled home encompasses modern luxuries with the characteristics of a French chateau, just moments away from Boston. This is a luxurious property built to offer a memorable experience with entertaining amenities for fourteen guests. Every detail has been considered, filled with natural light from all the large windows, furnished by Restoration Hardware, Viking Appliances, Quality Linens and many other high-end luxuries.

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Luxe

Home in Dennis Port

Cape Cod Oasis in Dennis | Pool, Spa, Fire Pit |

Escape to this Luxury 6BR/5BA Dennis Retreat featuring a heated pool, spa,sauna and firepit. Perfect for families or groups, the home offers spacious living areas, a fully equipped kitchen, and resort-style outdoor spaces. Just minutes from Cape Cod best beaches, dining, and activities, this property blends comfort, style, convenience for an unforgettable stay.roup will be comfortable in this spacious and unique space. POOL/SPA open 20th APril

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Luxe

The exterior of the house is viewed from an elevated angle, showcasing multiple levels with a light-colored facade. A spacious deck is visible, furnished with outdoor seating. Surrounding greenery and sandy areas lead to a view of the ocean in the background. Nearby homes are visible, highlighting the coastal setting.

Home in Sandwich

5.0 out of 5 average rating, 63 reviews

Waterfront home w/ Beach access

At Après Sea you are surrounded by natural beauty - Scorton Creek on the back of the house & East Sandwich Beach across the street from the front of the house. You'll love quiet walks on the beach, Cape Cod bay, and the sunrises & sunsets. The house is perfect for entertaining with an open air deck, covered deck, natural gas BBQ, chef's kitchen, and 5 TVs. Parking for up to 6 cars. Welcoming World Cup 2026 supporters!

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Luxe

An aerial view showcases a spacious outdoor area highlighted by a heated pool, surrounded by a patio with lounge chairs and green umbrellas. An outdoor dining table, accommodating up to 14 people, is positioned nearby, surrounded by lush landscaping and comfortable seating areas.

Home in Barnstable

5.0 out of 5 average rating, 19 reviews

Luxury Historic Estate with Expansive Grounds

Beautifully restored, this home is only 10 minutes away from Sandy Neck beach and has everything you need for your summer vacation. The outside space is also perfect for family get-togethers, as there is a heated pool , plenty of seating around the gas fireplace and an outdoor dining table large enough to seat 14 people! The lush landscaping throughout the property is sure to make you feel like you're in paradise!

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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

Home in Barnstable

Cape Cod Luxury Escape: Pool, Fire Pit & Family

Escape to your dream Cape Cod retreat! This luxurious 7-bedroom, 5.5-bathroom home boasts a private heated pool, fire pit, and game room, perfect for unforgettable family vacations or group getaways. Enjoy resort-style amenities and a prime location near beaches, attractions, and shopping in Barnstable, MA. Experience the best of Cape Cod living in this spacious and well-equipped house.

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