Luxury rentals in Massachusetts

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Top-rated vacation rentals in Massachusetts

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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

17–24 Sep

$5,841 SGD per night

Villa in Nantucket

5.0 out of 5 average rating, 5 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.

11–18 Dec

$3,193 SGD per night

Home in New Marlborough

Sunset Falls

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.

15–22 Nov

$4,783 SGD per night

Place to stay in Great Barrington

The Freeman Berkshires

Built in the 1800s, this Adirondack-style estate is set on 40 acres between New York and Boston in the Berkshires. Complete with a vineyard, games room, and private dock, there are plenty of ways to spend your days. If you’re up for adventure, there’s excellent skiing and hiking nearby. For a more relaxed getaway, sit and sip tea in the edible garden or catch up with a good book on the terrace. Copyright © Luxury Retreats. All rights reserved.

24–31 Dec

$3,543 SGD per night

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.

22–29 Mar

$6,915 SGD per night