Tuckahoe Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 18 - Aug 19
Tomorrow
Aug 19 - Aug 20
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Vacation Rentals in Tuckahoe

Newly Renovated Pristine Southampton Colonial
Exterior

Newly Renovated Pristine Southampton Colonial

9.8 out of 10, Exceptional, (11)
"This property worked great for us. Close to everywhere we need to be. Very clean as well."
Newly Renovated Pristine Southampton Colonial
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great location, great views. Walls are a little thin."
The price is ￥48,814
￥62,165 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is ￥39,079
￥76,935 total
includes taxes & fees
Aug 21 - Aug 22
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Walk to town, Bike to beach, Private pool oasis !
Outdoor pool

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (91)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Sag Harbor Suite by the Beach
1 bedroom, WiFi, bed sheets

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is ￥73,448
￥143,951 total
includes taxes & fees
Aug 19 - Aug 20
Southampton cozy cottage by the beach
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Fridge, microwave, oven, stovetop

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Exterior

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
A heated pool

2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!

10.0 out of 10, Exceptional, (87)
"It was a great stay"
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (185)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
The price is ￥78,820
￥138,148 total
includes taxes & fees
Sep 1 - Sep 2
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is ￥73,448
￥134,366 total
includes taxes & fees
Aug 19 - Aug 20
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is ￥29,788
￥38,406 total
includes taxes & fees
Aug 19 - Aug 20
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Tuckahoe Hotel Reviews

Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Our stay at Hampton’s Vacation Inn was excellent. The cottage was awesome, the staff was amazing, and the room was clean and very accessible to everything. I would definitely stay here again and highly recommend it to others."
Athanassios 3-night trip
Posted 6 hours ago
Hampton's Vacation Inn

Frequently asked questions

Are there vacation rentals in Tuckahoe?

Yes, you can find vacation rentals close to top points of interest in Tuckahoe, or you can go with a more secluded option if you're looking for a relaxing stay. Visitors to Tuckahoe speak positively about the beaches and coffeehouses in this destination. Make sure you have time to check out the golf courses and monuments during your trip.

What are some of the best vacation rentals in Tuckahoe?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This vacation home rental outside of Tuckahoe offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Tuckahoe?

Expedia has 53 vacation rentals for your stay in Tuckahoe.

What can I see and do in Tuckahoe?

While exploring the area, visit family-friendly sights like Railroad Museum of Long Island, or get outside and enjoy nature at The Hamptons Beaches. Other places in town to visit include Shinnecock Hills Golf Course and Sebonack Golf Course.

What are vacation rentals like in Tuckahoe?

Vacation rentals are private properties you can stay in for several days or more in Tuckahoe. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family gatherings.