Holiday rentals near Walking Dunes Trailhead
We found 2,663 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Walking Dunes Trailhead that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, such as parking and air conditioning. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Walking Dunes Trailhead
Showing deals for:31 Oct - 7 Nov
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
(8 reviews)
East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
East Hampton, NY
8% off
Price is AU$9,210
AU$9,210
AU$1,316 per night
includes taxes & fees
Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
1010 out of 10 rating
Exceptional
(12 reviews)
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
East Hampton, NY
7% off
Price is AU$14,218
AU$14,218
AU$2,031 per night
includes taxes & fees
Image gallery for Bright, open waterfront house with gorgeous sunsets and private beach
1010 out of 10 rating
Exceptional
(10 reviews)
Bright, open waterfront house with gorgeous sunsets and private beach
Shelter Island, NY
7% off
Price is AU$8,074
AU$8,074
AU$1,153 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$9,846
AU$9,846
AU$1,407 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
(10 reviews)
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
Southampton, NY
11% off
Price is AU$17,725
AU$17,725
AU$2,532 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$12,944
AU$12,944
AU$1,849 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$11,658
AU$11,658
AU$1,665 per night
includes taxes & fees
Image gallery for Perfect East Hampton Home for Families and friends! Last minute booking discount
1010 out of 10 rating
Exceptional
(8 reviews)
Perfect East Hampton Home for Families and friends! Last minute booking discount
East Hampton, NY
8% off
Price is AU$13,040
AU$13,040
AU$1,863 per night
includes taxes & fees
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$42,290
AU$42,290
AU$6,041 per night
includes taxes & fees
Image gallery for Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.
1010 out of 10 rating
Exceptional
(5 reviews)
Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.
Bridgehampton, NY
8% off
Price is AU$6,305
AU$6,305
AU$901 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$15,943
AU$15,943
AU$2,278 per night
includes taxes & fees
Image gallery for Lake House - Brand New, Renovation Just Completed
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Lake House - Brand New, Renovation Just Completed
Montauk, NY
8% off
Price is AU$30,052
AU$30,052
AU$4,293 per night
includes taxes & fees
Image gallery for Relax and Enjoy!
1010 out of 10 rating
Exceptional
(14 reviews)
Relax and Enjoy!
Shelter Island Heights, NY
8% off
Price is AU$13,326
AU$13,326
AU$1,904 per night
includes taxes & fees
Image gallery for Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
1010 out of 10 rating
Exceptional
(21 reviews)
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Sagaponack, NY
8% off
Price is AU$34,245
AU$34,245
AU$4,892 per night
includes taxes & fees
Image gallery for Charming East Hampton cottage w/pool, near Georgica beach
1010 out of 10 rating
Exceptional
(88 reviews)
Charming East Hampton cottage w/pool, near Georgica beach
East Hampton, NY
8% off
Price is AU$10,441
AU$10,441
AU$1,492 per night
includes taxes & fees
Image gallery for Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
Shelter Island, NY
8% off
Price is AU$9,809
AU$9,809
AU$1,401 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
(52 reviews)
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Southampton, NY
7% off
Price is AU$17,096
AU$17,096
AU$2,442 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$27,267
AU$27,267
AU$3,895 per night
includes taxes & fees
Image gallery for Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
1010 out of 10 rating
Exceptional
(94 reviews)
Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
Sag Harbor, NY
15% off
Price is AU$13,224
AU$13,224
AU$1,889 per night
includes taxes & fees
Image gallery for 5 Bedrooms, Heated Pool!
9.89.8 out of 10 rating
Exceptional
(54 reviews)
5 Bedrooms, Heated Pool!
Bridgehampton, NY
8% off
Price is AU$13,135
AU$13,135
AU$1,876 per night
includes taxes & fees
Image gallery for Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
1010 out of 10 rating
Exceptional
(19 reviews)
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
East Marion, NY
8% off
Price is AU$6,498
AU$6,498
AU$928 per night
includes taxes & fees
Image gallery for Hampton Beach Barn w/ Infrared Sauna and Heated Pool - Dog friendly.
1010 out of 10 rating
Exceptional
(17 reviews)
Hampton Beach Barn w/ Infrared Sauna and Heated Pool - Dog friendly.
Water Mill, NY
12% off
Price is AU$15,836
AU$15,836
AU$2,262 per night
includes taxes & fees
Image gallery for Beautiful, bright, heated pool, near beaches, villages, restaurants, Wolffer.
1010 out of 10 rating
Exceptional
(32 reviews)
Beautiful, bright, heated pool, near beaches, villages, restaurants, Wolffer.
Bridgehampton, NY
24% off
Price is AU$8,189
AU$8,189
AU$1,170 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
19% off
Price is AU$10,979
AU$10,979
AU$1,568 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Walking Dunes Trailhead
Showing deals for: 30 Oct - 2 Nov
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
25 reviews(25 reviews)
The current price is AU$4,964
AU$4,964
for 3 nights, 1 cottage
AU$1,655 per night
includes taxes & fees
Montauk House with Lake View
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
The current price is AU$4,096
AU$4,096
for 3 nights, 1 home
AU$1,365 per night
includes taxes & fees
4 bedroom 2.5 bath AC,Decks Pvt Beach,HotTub Seasonal FirePit 1-Week Min Summer
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
The current price is AU$6,247
AU$6,247
for 3 nights, 1 home
AU$2,082 per night
includes taxes & fees
Montauk, Hither Hills, 4 bedroom, private ocean access, beach house
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
The current price is AU$4,017
AU$4,017
for 3 nights, 1 home
AU$1,339 per night
includes taxes & fees
Montauk Retreat with Pool and Views of Lake Montauk
Sleeps 10 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
The current price is AU$7,035
AU$7,035
for 3 nights, 1 home
AU$2,345 per night
includes taxes & fees
Montauk Waterfront Studio With Breathtaking Sunset View
Sleeps 2 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
The current price is AU$1,620
AU$1,620
for 3 nights, 1 apartment
AU$540 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