
Holiday rentals near Shelter Island Historical Society
We found 3,738 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Shelter Island Historical Society, take a look at holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Shelter Island Historical Society
Showing deals for:28 Nov - 5 Dec
Image gallery for Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

1010 out of 10 rating
Exceptional
(6 reviews)
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Sag Harbor, NY
8% off
Price is AU$41,930
AU$41,930
AU$5,990 per night
includes taxes & fees
Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

1010 out of 10 rating
Exceptional
(13 reviews)
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
East Hampton, NY
7% off
Price is AU$14,075
AU$14,075
AU$2,011 per night
includes taxes & fees
Image gallery for Private Waterfront Home Dock, Kayaks

9.29.2 out of 10 rating
Wonderful
(19 reviews)
Private Waterfront Home Dock, Kayaks
Southold, NY
7% off
Price is AU$8,282
AU$8,282
AU$1,183 per night
includes taxes & fees
Image gallery for Sweet Cottage in Beach Community

1010 out of 10 rating
Exceptional
(11 reviews)
Sweet Cottage in Beach Community
Niantic, CT
8% off
Price is AU$3,111
AU$3,111
AU$444 per night
includes taxes & fees
Image gallery for Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

9.89.8 out of 10 rating
Exceptional
(25 reviews)
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Southampton, NY
12% off
Price is AU$20,461
AU$20,461
AU$2,923 per night
includes taxes & fees
Image gallery for Relax in Hampton Bays...

9.89.8 out of 10 rating
Exceptional
(72 reviews)
Relax in Hampton Bays...
Hampton Bays, NY
8% off
Price is AU$6,962
AU$6,962
AU$995 per night
includes taxes & fees
Image gallery for East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly

9.89.8 out of 10 rating
Exceptional
(9 reviews)
East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
East Hampton, NY
8% off
Price is AU$9,117
AU$9,117
AU$1,302 per night
includes taxes & fees
Image gallery for Cozy Seaside Cottage

1010 out of 10 rating
Exceptional
(37 reviews)
Cozy Seaside Cottage
New Suffolk, NY
11% off
Price is AU$8,291
AU$8,291
AU$1,184 per night
includes taxes & fees
Image gallery for HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

9.89.8 out of 10 rating
Exceptional
(10 reviews)
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
Southold, NY
8% off
Price is AU$24,254
AU$24,254
AU$3,465 per night
includes taxes & fees
Image gallery for Summer in the Hamptons

9.49.4 out of 10 rating
Exceptional
(13 reviews)
Summer in the Hamptons
East Hampton, NY
8% off
Price is AU$12,813
AU$12,813
AU$1,830 per night
includes taxes & fees
Image gallery for Private 2.1 acre gated home with heated pool and tennis & pickleball court

9.89.8 out of 10 rating
Exceptional
(20 reviews)
Private 2.1 acre gated home with heated pool and tennis & pickleball court
Southampton, NY
8% off
Price is AU$12,560
AU$12,560
AU$1,794 per night
includes taxes & fees
Image gallery for Hamptons Oasis with Heated Pool

1010 out of 10 rating
Exceptional
(11 reviews)
Hamptons Oasis with Heated Pool
Hampton Bays, NY
8% off
Price is AU$19,484
AU$19,484
AU$2,783 per night
includes taxes & fees
Image gallery for One Minute to Main St. East Hampton // Private Backyard Oasis

1010 out of 10 rating
Exceptional
(20 reviews)
One Minute to Main St. East Hampton // Private Backyard Oasis
East Hampton, NY
8% off
Price is AU$28,701
AU$28,701
AU$4,100 per night
includes taxes & fees
Image gallery for Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.89.8 out of 10 rating
Exceptional
(53 reviews)
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Southampton, NY
8% off
Price is AU$18,545
AU$18,545
AU$2,649 per night
includes taxes & fees
Image gallery for Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

1010 out of 10 rating
Exceptional
(6 reviews)
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Riverhead, NY
8% off
Price is AU$4,369
AU$4,369
AU$624 per night
includes taxes & fees
Image gallery for Ultimate Hamptons Vacation Mansion

1010 out of 10 rating
Exceptional
(10 reviews)
Ultimate Hamptons Vacation Mansion
Wainscott, NY
17% off
Price is AU$73,284
AU$73,284
AU$10,469 per night
includes taxes & fees
Image gallery for Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

1010 out of 10 rating
Exceptional
(35 reviews)
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Southold, NY
8% off
Price is AU$11,828
AU$11,828
AU$1,690 per night
includes taxes & fees
Image gallery for Charming East Hampton cottage w/pool, near Georgica beach

9.89.8 out of 10 rating
Exceptional
(90 reviews)
Charming East Hampton cottage w/pool, near Georgica beach
East Hampton, NY
8% off
Price is AU$10,335
AU$10,335
AU$1,476 per night
includes taxes & fees
Image gallery for Beautiful Renovated Beachfront Home

1010 out of 10 rating
Exceptional
(57 reviews)
Beautiful Renovated Beachfront Home
Greenport, NY
8% off
Price is AU$9,607
AU$9,607
AU$1,372 per night
includes taxes & fees
Image gallery for Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques

1010 out of 10 rating
Exceptional
(13 reviews)
Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques
Old Lyme, CT
8% off
Price is AU$23,221
AU$23,221
AU$3,317 per night
includes taxes & fees
Image gallery for Private oasis with new baths and heated Gunite pool near Wades Beach

1010 out of 10 rating
Exceptional
(32 reviews)
Private oasis with new baths and heated Gunite pool near Wades Beach
Shelter Island, NY
8% off
Price is AU$10,950
AU$10,950
AU$1,564 per night
includes taxes & fees
Image gallery for Huge private 4bdrm, 5 bath, house w/pool. Sleeps 10, near Gurneys! Pet friendly

9.89.8 out of 10 rating
Exceptional
(23 reviews)
Huge private 4bdrm, 5 bath, house w/pool. Sleeps 10, near Gurneys! Pet friendly
Montauk, NY
8% off
Price is AU$16,597
AU$16,597
AU$2,371 per night
includes taxes & fees
Image gallery for Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

1010 out of 10 rating
Exceptional
(12 reviews)
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Mattituck, NY
16% off
Price is AU$4,322
AU$4,322
AU$617 per night
includes taxes & fees
Image gallery for Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village

1010 out of 10 rating
Exceptional
(37 reviews)
Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village
Sag Harbor, NY
8% off
Price is AU$18,608
AU$18,608
AU$2,658 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Shelter Island Historical Society
Fairy Tale Guest Cottage in Magic Garden by Pool
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Charming Waterfront Cottage with Sunset Views!
Sleeps 7 · 4 bedrooms · 1+ bathroom
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Modern Luxury w/ Private Pool. 5 min from Beach & Town of Sag Harbor
Sleeps 10 · 5 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Designer home in a prime location - Close to wineries and Ocean Beaches
Sleeps 10 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
New and Modern Bridgehampton Accommodations
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Stunning Hampton Holiday Family Fantasy for your Team
Sleeps 10 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value