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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

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!

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.

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

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

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.

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!

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.

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!

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.

Cape Cod Family Vacation

Experience luxury and comfort in this stunning Cape Cod retreat. Perfect for families and groups, this beautifully designed home accommodates up to 12 guests with spacious living areas, elegant décor, and a relaxing coastal atmosphere. Enjoy unforgettable summer days and peaceful evenings while creating lasting memories with loved ones in one of the Cape’s most desirable destinations.

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