
Holiday rentals near Shelter Island Historical Society
We found 3,785 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:26 Sept - 3 Oct
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
(7 reviews)
East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
East Hampton, NY
8% off
Price is AU$9,093
AU$9,093
AU$1,299 per night
includes taxes & fees
Image gallery for Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!

9.69.6 out of 10 rating
Exceptional
(20 reviews)
Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
East Hampton, NY
17% off
Price is AU$41,971
AU$41,971
AU$5,996 per night
includes taxes & fees
Image gallery for Private Waterfront Home: Dock, Kayaks

9.29.2 out of 10 rating
Wonderful
(16 reviews)
Private Waterfront Home: Dock, Kayaks
Southold, New York
7% off
Price is AU$7,284
AU$7,284
AU$1,041 per night
includes taxes & fees
Image gallery for Book your vacation at our EH retreat on the water!

1010 out of 10 rating
Exceptional
(29 reviews)
Book your vacation at our EH retreat on the water!
East Hampton, NY
8% off
Price is AU$21,513
AU$21,513
AU$3,073 per night
includes taxes & fees
Image gallery for NEW LISTING! Chic, Affordably Priced Southampton home, convenient location.

1010 out of 10 rating
Exceptional
(6 reviews)
NEW LISTING! Chic, Affordably Priced Southampton home, convenient location.
Southampton, NY
8% off
Price is AU$11,601
AU$11,601
AU$1,657 per night
includes taxes & fees
Image gallery for Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

9.89.8 out of 10 rating
Exceptional
(25 reviews)
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
Southampton, NY
16% off
Price is AU$19,210
AU$19,210
AU$2,744 per night
includes taxes & fees
Image gallery for Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton

1010 out of 10 rating
Exceptional
(8 reviews)
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
Southampton, NY
8% off
Price is AU$15,450
AU$15,450
AU$2,207 per night
includes taxes & fees
Image gallery for New and Modern Bridgehampton Accommodations

1010 out of 10 rating
Exceptional
(8 reviews)
New and Modern Bridgehampton Accommodations
Bridgehampton, NY
6% off
Price is AU$4,642
AU$4,642
AU$663 per night
includes taxes & fees
Image gallery for Hamptons Oasis with Heated Pool

9.89.8 out of 10 rating
Exceptional
(7 reviews)
Hamptons Oasis with Heated Pool
Hampton Bays, NY
8% off
Price is AU$19,223
AU$19,223
AU$2,746 per night
includes taxes & fees
Image gallery for WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE

1010 out of 10 rating
Exceptional
(5 reviews)
WALK TO BEACH - HAMPTONS WITHOUT THE HASSLE
Hampton Bays, NY
8% off
Price is AU$8,910
AU$8,910
AU$1,273 per night
includes taxes & fees
Image gallery for Summer in the Hamptons

9.29.2 out of 10 rating
Wonderful
(12 reviews)
Summer in the Hamptons
East Hampton, NY
8% off
Price is AU$10,244
AU$10,244
AU$1,463 per night
includes taxes & fees
Image gallery for Heated Pool + Hot Tub - Luxe 7BR Villa

1010 out of 10 rating
Exceptional
(18 reviews)
Heated Pool + Hot Tub - Luxe 7BR Villa
Hampton Bays, NY
9% off
Price is AU$35,814
AU$35,814
AU$5,116 per night
includes taxes & fees
Image gallery for Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.68.6 out of 10 rating
Excellent
(25 reviews)
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Montauk, NY
8% off
Price is AU$12,997
AU$12,997
AU$1,857 per night
includes taxes & fees
Image gallery for Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

1010 out of 10 rating
Exceptional
(8 reviews)
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
Sag Harbor, NY
8% off
Price is AU$19,433
AU$19,433
AU$2,776 per night
includes taxes & fees
Image gallery for Poppy's Hampton House: Big Yard, Beach, Renovated

9.89.8 out of 10 rating
Exceptional
(11 reviews)
Poppy's Hampton House: Big Yard, Beach, Renovated
Hampton Bays, New York
7% off
Price is AU$8,585
AU$8,585
AU$1,226 per night
includes taxes & fees
Image gallery for Incredible Location, Family and Dog Friendly , minutes to flying point

9.49.4 out of 10 rating
Exceptional
(15 reviews)
Incredible Location, Family and Dog Friendly , minutes to flying point
Water Mill, NY
8% off
Price is AU$25,624
AU$25,624
AU$3,661 per night
includes taxes & fees
Image gallery for Bright, light home w/ modern kitchen, 4-5 minute drive to East Hampton Village!

1010 out of 10 rating
Exceptional
(7 reviews)
Bright, light home w/ modern kitchen, 4-5 minute drive to East Hampton Village!
East Hampton, NY
17% off
Price is AU$7,217
AU$7,217
AU$1,031 per night
includes taxes & fees
Image gallery for Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

9.49.4 out of 10 rating
Exceptional
(6 reviews)
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Orient, NY
8% off
Price is AU$24,078
AU$24,078
AU$3,440 per night
includes taxes & fees
Image gallery for Bridgehampton Breeze

9.29.2 out of 10 rating
Wonderful
(9 reviews)
Bridgehampton Breeze
Bridgehampton, NY
14% off
Price is AU$22,532
AU$22,532
AU$3,219 per night
includes taxes & fees
Image gallery for Prime East Hampton Village Location. Heated Pool. Walk To All!

1010 out of 10 rating
Exceptional
(16 reviews)
Prime East Hampton Village Location. Heated Pool. Walk To All!
East Hampton, NY
16% off
Price is AU$12,483
AU$12,483
AU$1,783 per night
includes taxes & fees
Image gallery for Chic Modern Private Designer 1.5 Acre Private Oasis

1010 out of 10 rating
Exceptional
(6 reviews)
Chic Modern Private Designer 1.5 Acre Private Oasis
East Hampton, NY
30% off
Price is AU$23,714
AU$23,714
AU$3,388 per night
includes taxes & fees
Image gallery for Charming East Hampton cottage w/pool, near Georgica beach

1010 out of 10 rating
Exceptional
(86 reviews)
Charming East Hampton cottage w/pool, near Georgica beach
East Hampton, NY
8% off
Price is AU$11,974
AU$11,974
AU$1,711 per night
includes taxes & fees
Image gallery for 125+Acre Nature Preserve Enveloped Sag Harbor Home, 5 BED, 5.5 BATH, POOL

1010 out of 10 rating
Exceptional
(9 reviews)
125+Acre Nature Preserve Enveloped Sag Harbor Home, 5 BED, 5.5 BATH, POOL
East Hampton, NY
8% off
Price is AU$23,187
AU$23,187
AU$3,312 per night
includes taxes & fees
Image gallery for Stunning Home w/ Gorgeous Pool & Grounds. Gas grill. Walk to water, sunsets!

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Stunning Home w/ Gorgeous Pool & Grounds. Gas grill. Walk to water, sunsets!
East Hampton, NY
19% off
Price is AU$7,993
AU$7,993
AU$1,142 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Shelter Island Historical Society
Showing deals for: 23 Sept - 26 Sept9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Sleeps 28 · 9 bedrooms · 9+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
The current price is AU$14,160
AU$14,160
for 3 nights, 1 home
AU$4,720 per night
includes taxes & fees
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
55 reviews(55 reviews)
The current price is AU$6,441
AU$6,441
for 3 nights, 1 home
AU$2,147 per night
includes taxes & fees
Fairy Tale Guest Cottage in Magic Garden by Pool
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
The current price is AU$1,889
AU$1,889
for 3 nights, 1 cottage
AU$630 per night
includes taxes & fees
Charming Waterfront Cottage with Sunset Views!
Sleeps 7 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$5,646
AU$5,646
for 3 nights, 1 home
AU$1,882 per night
includes taxes & fees
Stunning Hampton Holiday Family Fantasy for your Team
Sleeps 10 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
The current price is AU$11,532
AU$11,532
for 3 nights, 1 home
AU$3,844 per night
includes taxes & fees
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
The current price is AU$6,508
AU$6,508
for 3 nights, 1 home
AU$2,169 per night
includes taxes & fees
- 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