Holiday rentals near Walking Dunes Trailhead
We found 2,636 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:19 Sept - 26 Sept
Image gallery for Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
1010 out of 10 rating
Exceptional
(93 reviews)
Waterfront, Pool, HotTub, Strong WIFI, Pingpong, Paddleboard, Kayak, Bocce Court
Sag Harbor, NY
8% off
Price is NZ$25,194
NZ$25,194
NZ$3,599 per night
includes taxes & fees
Image gallery for Modern East Hampton w/ Private Pool and Tennis
1010 out of 10 rating
Exceptional
(48 reviews)
Modern East Hampton w/ Private Pool and Tennis
East Hampton, NY
8% off
Price is NZ$24,138
NZ$24,138
NZ$3,448 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
28% off
Price is NZ$20,150
NZ$20,150
NZ$2,879 per night
includes taxes & fees
Image gallery for Luxurious Private 5-Bedroom Montauk Beach Family Home
1010 out of 10 rating
Exceptional
(25 reviews)
Luxurious Private 5-Bedroom Montauk Beach Family Home
Montauk, NY
8% off
Price is NZ$30,281
NZ$30,281
NZ$4,326 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
16% off
Price is NZ$82,927
NZ$82,927
NZ$11,847 per night
includes taxes & fees
Image gallery for Quiet Family Friendly Hideaway With Pool And Poolhouse
1010 out of 10 rating
Exceptional
(44 reviews)
Quiet Family Friendly Hideaway With Pool And Poolhouse
East Hampton, NY
8% off
Price is NZ$23,071
NZ$23,071
NZ$3,296 per night
includes taxes & fees
Image gallery for Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
9.89.8 out of 10 rating
Exceptional
(84 reviews)
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Sag Harbor, NY
16% off
Price is NZ$17,664
NZ$17,664
NZ$2,523 per night
includes taxes & fees
Image gallery for One Minute to Main St. East Hampton // Private Backyard Oasis
1010 out of 10 rating
Exceptional
(19 reviews)
One Minute to Main St. East Hampton // Private Backyard Oasis
East Hampton, NY
8% off
Price is NZ$19,912
NZ$19,912
NZ$2,845 per night
includes taxes & fees
Image gallery for Cove View Manor of Sag Harbor
1010 out of 10 rating
Exceptional
(67 reviews)
Cove View Manor of Sag Harbor
Sag Harbor, NY
7% off
Price is NZ$20,016
NZ$20,016
NZ$2,859 per night
includes taxes & fees
Image gallery for Escape to Sag Harbor
1010 out of 10 rating
Exceptional
(47 reviews)
Escape to Sag Harbor
Sag Harbor, NY
8% off
Price is NZ$13,419
NZ$13,419
NZ$1,917 per night
includes taxes & fees
Image gallery for Beautiful designer modern luxury home - steps from beach
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful designer modern luxury home - steps from beach
East Hampton, NY
12% off
Price is NZ$16,638
NZ$16,638
NZ$2,377 per night
includes taxes & fees
Image gallery for Beautiful Home Heated Pool Family Setting Pets Ok Amazing Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Beautiful Home Heated Pool Family Setting Pets Ok Amazing Location
East Hampton, NY
12% off
Price is NZ$17,876
NZ$17,876
NZ$2,554 per night
includes taxes & fees
Image gallery for Ultimate Hamptons Vacation Estate
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Ultimate Hamptons Vacation Estate
Sag Harbor, NY
21% off
Price is NZ$75,675
NZ$75,675
NZ$10,811 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
14% off
Price is NZ$8,216
NZ$8,216
NZ$1,174 per night
includes taxes & fees
Image gallery for Perfect Family home, AC, Heated Pool, 3BR 2Bath
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Perfect Family home, AC, Heated Pool, 3BR 2Bath
East Hampton, NY
21% off
Price is NZ$11,230
NZ$11,230
NZ$1,604 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
7% off
Price is NZ$29,059
NZ$29,059
NZ$4,151 per night
includes taxes & fees
Image gallery for BIG July DISCOUNT Resort style backyard including professional PICKLEBALL COURT.
9.89.8 out of 10 rating
Exceptional
(54 reviews)
BIG July DISCOUNT Resort style backyard including professional PICKLEBALL COURT.
Southampton, NY
8% off
Price is NZ$16,681
NZ$16,681
NZ$2,383 per night
includes taxes & fees
Image gallery for Private Hamptons cottage in ideal Amagansett location
1010 out of 10 rating
Exceptional
(16 reviews)
Private Hamptons cottage in ideal Amagansett location
Amagansett, NY
8% off
Price is NZ$9,420
NZ$9,420
NZ$1,346 per night
includes taxes & fees
Image gallery for Large East Hampton house with heated pool and home gym - fully fenced
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Large East Hampton house with heated pool and home gym - fully fenced
East Hampton, NY
16% off
Price is NZ$20,490
NZ$20,490
NZ$2,927 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
18% off
Price is NZ$8,762
NZ$8,762
NZ$1,252 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 NZ$11,525
NZ$11,525
NZ$1,646 per night
includes taxes & fees
Image gallery for ⚡️ Sag Harbor Gem, $15K any 2 weeks in July or August!! Prime location, Pool
1010 out of 10 rating
Exceptional
(49 reviews)
⚡️ Sag Harbor Gem, $15K any 2 weeks in July or August!! Prime location, Pool
Sag Harbor, NY
16% off
Price is NZ$11,541
NZ$11,541
NZ$1,649 per night
includes taxes & fees
Image gallery for Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!
1010 out of 10 rating
Exceptional
(34 reviews)
Out Door Theater Fire Pit Bocce court- WATCH VIDEO!!!
East Hampton, NY
8% off
Price is NZ$14,398
NZ$14,398
NZ$2,057 per night
includes taxes & fees
Image gallery for Hamptons Beach House w/ Pool, Chef's Kitchen, Wi-Fi, AC , WFH desk area
1010 out of 10 rating
Exceptional
(24 reviews)
Hamptons Beach House w/ Pool, Chef's Kitchen, Wi-Fi, AC , WFH desk area
East Hampton, NY
8% off
Price is NZ$9,457
NZ$9,457
NZ$1,351 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: 13 Sept - 16 Sept
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 NZ$7,963
NZ$7,963
for 3 nights, 1 cottage
NZ$2,654 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
20 reviews(20 reviews)
The current price is NZ$7,996
NZ$7,996
for 3 nights, 1 home
NZ$2,665 per night
includes taxes & fees
Offshore Montauk
Sleeps 3 · 1 bedroom
The current price is NZ$3,395
NZ$3,395
for 3 nights, 1 room
NZ$1,132 per night
includes taxes & fees
Newly Renovated Montauk Condo with Ocean Views!
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
The current price is NZ$2,817
NZ$2,817
for 3 nights, 1 apartment
NZ$939 per night
includes taxes & fees
Montauk House with Lake View
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
The current price is NZ$6,399
NZ$6,399
for 3 nights, 1 home
NZ$2,133 per night
includes taxes & fees
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Sleeps 4 · 1 bedroom · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
The current price is NZ$2,792
NZ$2,792
for 3 nights, 1 apartment
NZ$931 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