The 30 Best Holiday home rentals in Nantucket, Massachusetts

Nantucket Rentals is a premier real estate and travel agency located at 53 Main Street in Nantucket, Massachusetts. We specialize in providing luxurious vacation rentals on the picturesque island of Nantucket. Our team of experienced agents will help you find the perfect rental property for your next getaway, whether you're looking for a cozy cottage by the beach or a spacious waterfront estate. With our local expertise and personalized service, we ensure that your Nantucket vacation is unforgettable. Contact us today to start planning your dream vacation on this charming island.

Faraway Nantucket is a charming lodging institution located at 29 Centre Street in the picturesque island of Nantucket, Massachusetts. This cozy retreat offers a peaceful and tranquil atmosphere, perfect for those looking to escape the hustle and bustle of everyday life. The accommodations at Faraway Nantucket are comfortable and inviting, providing guests with a home away from home during their stay. With its convenient location in the heart of Nantucket, guests can easily explore the island's many attractions, including beautiful beaches, historic sites, and charming shops and restaurants. Whether you're seeking a romantic getaway or a relaxing vacation with family and friends, Faraway Nantucket is the perfect choice for your next escape.

The Cottages at Nantucket Boat Basin is a charming lodging option located at 24 Old South Wharf in Nantucket, Massachusetts. This unique institution offers cozy cottages with stunning views of the marina, perfect for a relaxing getaway. As a real estate agency, they also offer opportunities to invest in waterfront properties in this picturesque location. Additionally, as a travel agency, they can help plan your dream vacation to Nantucket, ensuring a memorable experience. Whether you're looking for a weekend retreat or a long-term investment, The Cottages at Nantucket Boat Basin has everything you need for a perfect stay in this beautiful coastal town.

Perfect Cape Escape, Vacation Rental is a charming retreat located at 4 Coffey Lane in Dennis, Massachusetts. This real estate and travel agency offers a bright and spacious open concept with 4 beautiful bedrooms, perfect for a relaxing getaway. The large entertaining deck overlooks the expansive backyard, complete with a stone fire pit and outdoor shower for ultimate relaxation. Situated just minutes away from Swan Pond, Main Street, and Nantucket Sound, this vacation rental is in the perfect location for exploring all that Cape Cod has to offer. The property is nestled in a quiet and friendly residential neighborhood, just off route 28. Guests can easily walk to kayaking on Swan Pond River or grab a coffee at Dunkin Donuts. Within a short drive, guests can enjoy the beautiful beaches of Dennis, such as South Village Beach and Sea Street Beach. Nearby convenience stores, shopping plazas, and a variety of shops make it easy to find everything you need for a comfortable stay.

White Glove Services of Nantucket is a premier institution located at 2 Greglen Avenue in Nantucket, Massachusetts. We provide top-notch, personalized services to meet all of your needs with the utmost care and attention to detail. Our team of professionals is dedicated to ensuring your satisfaction and exceeding your expectations. Whether you require cleaning, organizing, or concierge services, we are here to cater to you with a white-glove touch. Experience luxury and excellence with White Glove Services of Nantucket.

Located at 135 South Shore Drive in Yarmouth, Massachusetts, Seaside Cottages offers a relaxing getaway on the oceanfront with a private beach overlooking Nantucket Sound. Our five-acre cottage colony is the perfect destination for couples and families looking to unwind and enjoy the beauty of Cape Cod. When you book directly with us, you won't have to worry about any additional booking or cleaning fees. Take advantage of our May special - stay 2 nights and get the 3rd night free! Or plan your fall getaway with our fall special - stay 2 nights and get the 3rd night 50% off. Just make sure to book online and note that blackout dates apply.

Located at 29 Main Street in Orleans, Massachusetts, WeNeedaVacation.com is a premier institution offering lodging, real estate, and travel services. Specializing in vacation rentals on Cape Cod, Martha's Vineyard, and Nantucket since 1997, we provide a wide range of options for travelers looking to explore the beautiful beaches, natural landscapes, and unique history of these iconic destinations. From historic Plymouth to the tip of Provincetown, the Cape offers an unparalleled combination of beauty and fun activities. Martha's Vineyard Island boasts six charming towns and 110 square miles of natural beauty, while Nantucket features a preserved main town surrounded by picturesque seaside communities. We offer flexible-length plans with no hidden fees or commissions, guaranteeing booking results and providing personalized services and resources for our members. As the go-to rental site for the Cape & Islands, WeNeedaVacation.com ensures a memorable and stress-free vacation experience. For added protection, travelers can also obtain instant travel insurance quotes through our website.

Southcape Resort and Club is a lodging institution located at 950 Falmouth Road in Mashpee, Massachusetts, United States. Situated in one of the most beautiful areas in Cape Cod, Mashpee attracts visitors year-round with its stunning beaches and bay access. The town is known for its fishing and boating community, as well as its proximity to Martha's Vineyard and Nantucket. The resort offers two-bedroom accommodations in either a townhouse or ranch style, each equipped with a fully equipped kitchen and spacious living and dining area. Guests can enjoy resort-style amenities such as five tennis courts, shuffleboard courts, indoor and outdoor pools, and a children's playground. With over thirty golf courses, luxury shopping, delicious restaurants, outdoor activities, and nightlife nearby, Southcape Resort and Club is the perfect home base for exploring all that Mashpee has to offer. Visitors can take advantage of special deals when booking directly with the resort. Whether you're looking to relax by the pool or explore the area's attractions, Southcape Resort and Club has something for everyone.

The Summer House India Street is a charming lodging institution located at 31 India Street in the picturesque town of Nantucket, Massachusetts. Situated in a historic building, this cozy retreat offers guests a peaceful and relaxing atmosphere for their summer getaway. With comfortable accommodations and a convenient location near the island's attractions, The Summer House India Street is the perfect choice for those looking to experience the beauty of Nantucket. Immerse yourself in the island's rich history and natural beauty while staying at this lovely establishment.

The Summer House Fair Street is a charming lodging institution located at 27 Fair Street in the picturesque town of Nantucket, Massachusetts. This historic establishment offers a cozy and inviting atmosphere for guests looking to experience the beauty and tranquility of the island. With comfortable accommodations, friendly staff, and a convenient location near the beach and downtown area, The Summer House Fair Street is the perfect choice for a relaxing getaway on Nantucket. Whether you're looking for a romantic retreat or a family vacation, this charming inn has everything you need for a memorable stay.

3 Hussey Street Guest House is a charming lodging located in the heart of Nantucket, Massachusetts. Situated at the address 3 Hussey Street, this guest house offers a cozy and inviting atmosphere for travelers looking to experience the beauty and history of Nantucket. With comfortable accommodations and a convenient location near shops, restaurants, and attractions, 3 Hussey Street Guest House is the perfect home base for exploring all that Nantucket has to offer. Whether you're visiting for a weekend getaway or an extended stay, you'll feel right at home at this welcoming guest house.

The Carriage House is a charming lodging establishment located at 5 Ray's Court in Nantucket, Massachusetts. This historic building offers a cozy and comfortable stay for guests looking to experience the beauty and charm of Nantucket. With its quaint architecture and prime location, the Carriage House provides a peaceful retreat for visitors to relax and unwind. Whether you're exploring the island's beaches, shops, or restaurants, the Carriage House is the perfect home base for your Nantucket getaway.

By The Sea Guests is a charming lodging institution located at 57 Chase Avenue in Dennis, Massachusetts, United States. Nestled on the beach, our guest rooms offer one or two beds, private bathrooms, TVs, and mini fridges, with most rooms boasting oceanfront or partial ocean views. With 12 guest rooms in the inn, guests can enjoy a comfortable stay with breakfast included seasonally from May through October. For those seeking more space and amenities, our Suites feature open-concept layouts with full kitchens, living rooms, private bathrooms, and private decks or balconies with side partial ocean views. We offer three one-bedroom suites and two two-bedroom suites, perfect for families or larger groups. Breakfast is not included but can be purchased during peak season.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

The Wade Cottages offer charming and cozy accommodations in the heart of Nantucket, Massachusetts. Located at 35 Shell Street, this quaint lodging option provides a peaceful and relaxing atmosphere for guests to enjoy their stay on the island. The cottages are tastefully decorated and equipped with all the amenities needed for a comfortable and enjoyable vacation. Whether you're looking for a romantic getaway or a family-friendly retreat, The Wade Cottages are the perfect choice for your stay in Nantucket.

Coast is a charming home goods store located at 54 1/2 Old South Road in Nantucket, Massachusetts. This store offers a curated selection of coastal-inspired decor, furniture, and accessories that will bring a touch of seaside charm to any home. From nautical accents to beachy textiles, Coast is the perfect place to find unique pieces that will add a touch of coastal living to your space. Whether you're looking to redecorate your beach house or simply want to bring a bit of the ocean into your home, Coast has everything you need to create a coastal-inspired oasis. Visit us today and let us help you bring the beauty of the coast into your home.