Holiday rentals near Walking Dunes Trailhead
We found 2,643 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:18 Jul - 25 Jul
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$28,777
NZ$28,777
NZ$4,111 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
(83 reviews)
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Sag Harbor, NY
17% off
Price is NZ$31,333
NZ$31,333
NZ$4,476 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$23,065
NZ$23,065
NZ$3,295 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
12% off
Price is NZ$17,680
NZ$17,680
NZ$2,526 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$29,980
NZ$29,980
NZ$4,283 per night
includes taxes & fees
Image gallery for Clearwater Beach Retreat - Perfect Family Beach House That Sleeps Six

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Clearwater Beach Retreat - Perfect Family Beach House That Sleeps Six
East Hampton, NY
20% off
Price is NZ$13,432
NZ$13,432
NZ$1,919 per night
includes taxes & fees
Image gallery for Bright and airy beach house - Water views, Beautiful Sunsets and Pool

1010 out of 10 rating
Exceptional
(16 reviews)
Bright and airy beach house - Water views, Beautiful Sunsets and Pool
Montauk, NY
8% off
Price is NZ$45,504
NZ$45,504
NZ$6,501 per night
includes taxes & fees
Image gallery for LUXE Fam Friendly 5 Bed Pool + Playground + Firepit + All Beach Gear + BBQ

1010 out of 10 rating
Exceptional
(11 reviews)
LUXE Fam Friendly 5 Bed Pool + Playground + Firepit + All Beach Gear + BBQ
East Hampton, NY
8% off
Price is NZ$41,199
NZ$41,199
NZ$5,886 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$57,974
NZ$57,974
NZ$8,282 per night
includes taxes & fees
Image gallery for Modern New Kitchen, Heated Pool! Walk to everything in East Hampton Village!

9.89.8 out of 10 rating
Exceptional
(31 reviews)
Modern New Kitchen, Heated Pool! Walk to everything in East Hampton Village!
East Hampton, NY
12% off
Price is NZ$25,750
NZ$25,750
NZ$3,679 per night
includes taxes & fees
Image gallery for New Fully Remodeled Post Modern Home, Perfect getaway for a family!

1010 out of 10 rating
Exceptional
(14 reviews)
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Water Mill, NY
8% off
Price is NZ$30,288
NZ$30,288
NZ$4,327 per night
includes taxes & fees
Image gallery for Idyllic Beach Front Access Cottage, East Hampton

1010 out of 10 rating
Exceptional
(6 reviews)
Idyllic Beach Front Access Cottage, East Hampton
East Hampton, NY
8% off
Price is NZ$20,920
NZ$20,920
NZ$2,989 per night
includes taxes & fees
Image gallery for Dreaming of summer fun or an off-season adventure? Enjoy both!

1010 out of 10 rating
Exceptional
(18 reviews)
Dreaming of summer fun or an off-season adventure? Enjoy both!
Water Mill, NY
8% off
Price is NZ$21,177
NZ$21,177
NZ$3,025 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
16% off
Price is NZ$60,350
NZ$60,350
NZ$8,621 per night
includes taxes & fees
Image gallery for Stunning, modern home with all new baths and heated Gunite pool near Wades Beach

1010 out of 10 rating
Exceptional
(28 reviews)
Stunning, modern home with all new baths and heated Gunite pool near Wades Beach
Shelter Island, NY
8% off
Price is NZ$16,759
NZ$16,759
NZ$2,394 per night
includes taxes & fees
Image gallery for Beautiful East Hampton Home

1010 out of 10 rating
Exceptional
(57 reviews)
Beautiful East Hampton Home
East Hampton, NY
8% off
Price is NZ$24,744
NZ$24,744
NZ$3,535 per night
includes taxes & fees
Image gallery for 8/6-8/13 special Prime Wainscott Estate South of Highway

1010 out of 10 rating
Exceptional
(7 reviews)
8/6-8/13 special Prime Wainscott Estate South of Highway
Wainscott, NY
8% off
Price is NZ$38,851
NZ$38,851
NZ$5,550 per night
includes taxes & fees
Image gallery for EH VILLAGE: WALK TO RESTAURANTS, BIKE TO BEACH!

1010 out of 10 rating
Exceptional
(11 reviews)
EH VILLAGE: WALK TO RESTAURANTS, BIKE TO BEACH!
East Hampton, NY
8% off
Price is NZ$17,985
NZ$17,985
NZ$2,569 per night
includes taxes & fees
Image gallery for Beautiful SagHarbour Village W/Heated pool 5 min walk to Beach/Restaurant/Museum

1010 out of 10 rating
Exceptional
(45 reviews)
Beautiful SagHarbour Village W/Heated pool 5 min walk to Beach/Restaurant/Museum
Sag Harbor, NY
8% off
Price is NZ$30,635
NZ$30,635
NZ$4,376 per night
includes taxes & fees
Image gallery for Spacious Culloden house

1010 out of 10 rating
Exceptional
(40 reviews)
Spacious Culloden house
Montauk, NY
50% off
Price is NZ$16,754
NZ$16,754
NZ$2,393 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 NZ$27,511
NZ$27,511
NZ$3,930 per night
includes taxes & fees
Image gallery for Everything in Hamptons special discount available for weekly and monthly renters

1010 out of 10 rating
Exceptional
(7 reviews)
Everything in Hamptons special discount available for weekly and monthly renters
Water Mill, NY
8% off
Price is NZ$115,155
NZ$115,155
NZ$16,451 per night
includes taxes & fees
Image gallery for Close to Montauk/ East Hapmton/Springs Getaway

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Close to Montauk/ East Hapmton/Springs Getaway
East Hampton, NY
8% off
Price is NZ$19,125
NZ$19,125
NZ$2,732 per night
includes taxes & fees
Image gallery for Bridgehampton Breeze

9.29.2 out of 10 rating
Wonderful
(9 reviews)
Bridgehampton Breeze
Bridgehampton, NY
8% off
Price is NZ$34,584
NZ$34,584
NZ$4,941 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Walking Dunes Trailhead
Iconic Mystic Mansion
Sleeps 14 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
4 bedroom 2.5 bath AC,Decks Pvt Beach,HotTub Seasonal FirePit 1-Week Min Summer
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Sleeps 12 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
99 reviews(99 reviews)
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)
Luxury Home-spectacular Water View, Sunsets, Gorgeous Pool, Direct Water Access
Sleeps 15 · 6 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 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