Winter Vacation Rentals & Cabin Rentals in Nantucket, MA

Compare 2,914 available beachfront holiday vacation home properties, starts from $29

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Nantucket, MA: Top Deals

76 Main
76 Main
76 Main
76 Main
76 Main
76 Main
4.6 (43 reviews)
76 Main
Hotel
$189 /night
View deal
Hotel Pippa
Hotel Pippa
Hotel Pippa
Hotel Pippa
Hotel Pippa
Hotel Pippa
Hotel Pippa
4.5 (102 reviews)
Hotel Pippa
Hotel
$179 /night
View deal
Greydon House
Greydon House
Greydon House
Greydon House
Greydon House
Greydon House
Greydon House
Greydon House
4.5 (75 reviews)
Greydon House
House
$149 /night
View deal
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
4.9 (100 reviews)
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Cottage · 6 Guests · 2 Bedrooms
$350 /night*
View deal
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
5.0 (37 reviews)
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Cottage · 4 Guests · 1 Bedroom
$315 /night*
View deal
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
4.9 (7 reviews)
New House in Convenient, Tranquil Setting Surrounded by Conservation Land
House · 8 Guests · 3 Bedrooms
$625 /night*
View deal
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
The Oak bluffs cottage, Martha’s Vineyard Island.
4.6 (12 reviews)
The Oak bluffs cottage, Martha’s Vineyard Island.
Guest House · 4 Guests · 2 Bedrooms
$250 /night*
View deal
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
5.0 (19 reviews)
Luxurious Harbor View “Cindy” cottage. Walk & bike to everything!
Cottage · 4 Guests · 1 Bedroom
$315 /night*
View deal
The Beachside
The Beachside
The Beachside
The Beachside
The Beachside
The Beachside
The Beachside
4.2 (296 reviews)
The Beachside
Hotel
$175 /night
View deal
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Similar Inspirational Vacation Rental Destinations

How Does The Vacation Home Rental Price Look Like in Nantucket, MA?
Vacation House & Cottage Rental Price Information in Nantucket, MA
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The graph shows the percentages of vacation homes in each price bucket. Nantucket has the largest percentage (52.20%) of homes in $500+ price range.
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What are some of the best activities, communities, and places of interest for snowbirds in Nantucket, MA?
Top Places for Snowbirds in Nantucket, MA
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Nantucket is an ideal place for snowbirds due to its proximity to healthcare, numerous attractions, and year-round mild climate. It’s also home to a vibrant senior community with plenty of social clubs and events to attend. With its stunning beaches, whale watching opportunities, and charming downtown area, it’s no surprise that many seniors choose to spend their winters here.

  • Cisco Brewers

    This brewery offers tastings and tours as well as light bites and live music. The outdoor beer garden is perfect for enjoying the sunny days, and there are even weekly yoga classes onsite.

  • Whaling Museum

    The Whaling Museum is the perfect location for learning about the island's past. Its interactive exhibits provide visitors with an immersive experience, and you can even take part in fun scavenger hunts.

  • Sankaty Head Golf Club

    This 18-hole golf club is located atop the highest point on Nantucket Island and provides breathtaking views from every hole. There's also a pro shop and two practice greens for members to use.

How Many Rental Accommodations Are Pets Friendly in Nantucket, MA?
Pets Allowed vs Not Allowed in Nantucket, MA
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21.00% of vacation homes in Nantucket are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
What Are The Must-Visit Places in Nantucket, MA?
Destinations To Visit During the Winter in Nantucket, MA
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What are the Airports in Nantucket, MA?
Suggested Airports in Nantucket, MA
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Here are the airports that located near Nantucket:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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