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Wainscott Woods Vacation Rentals

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Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Wainscott Woods Vacation Homes

Our top choices for Wainscott Woods vacation homes

Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is CA $18,608
CA $22,759 total
includes taxes & fees
Aug 30 - Aug 31
Stunning Southampton Village Modern Home
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is CA $6,823
CA $9,622 total
includes taxes & fees
Sep 10 - Sep 11
Sag Harbor Water View w Dock 1.5ml from town
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Terrace/patio

Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is CA $11,206
CA $16,678 total
includes taxes & fees
Aug 31 - Sep 1
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Aqua by American Beech - Rooftop Suite
Terrace/patio

Aqua by American Beech - Rooftop Suite

10.0 out of 10, Exceptional, (1)
"Quick stay after a day at the wineries. Location is is set in a beautiful quiet area and the view is just amazing. The staff could truly not be any better, any request or issue was dealt with in literally a minute. Room was perfect, clean and made you feel at home with anything you needed. Will definitely be back!"
The price is CA $605
CA $850 total
includes taxes & fees
Sep 9 - Sep 10
Aqua by American Beech - Rooftop Suite
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
9.6 out of 10, Exceptional, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is CA $304
CA $640 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is CA $5,514
CA $8,873 total
includes taxes & fees
Sep 3 - Sep 4
Spacious 5-bedroom house with water views and 2 houses from the bay.
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
The price is CA $3,712
CA $5,951 total
includes taxes & fees
Sep 23 - Sep 24
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is CA $827
CA $1,594 total
includes taxes & fees
Sep 2 - Sep 3
Beautifully farmhouse
September is the New August!
Outdoor pool, a heated pool

September is the New August!

10.0 out of 10, Exceptional, (88)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
The price is CA $2,423
CA $4,582 total
includes taxes & fees
Sep 3 - Sep 4
September is the New August!
Work and Play Special! Extended Stay Discount
Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is CA $1,107
CA $1,987 total
includes taxes & fees
Sep 14 - Sep 15
Work and Play Special! Extended Stay Discount
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Outdoor pool, a heated pool

Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons

10.0 out of 10, Exceptional, (57)
"We had a very nice stay at Stan's house. We spent the majority of our time relaxing in the beautiful backyard. The pool is amazing!"
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Bay Access Cottage + Pilates Gym
Beach nearby, sun loungers, beach towels

Bay Access Cottage + Pilates Gym

2.0 star property
The price is CA $563
CA $892 total
includes taxes & fees
Sep 9 - Sep 10
Bay Access Cottage + Pilates Gym
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. "
Southampton cozy cottage by the beach
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A heated pool

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

10.0 out of 10, Exceptional, (14)
"We loved our stay! The place is beautiful, quiet and located very close to Main St in Southampton. The host was extremely helpful and responsive."
The price is CA $2,164
CA $3,103 total
includes taxes & fees
Sep 3 - Sep 4
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is CA $329
CA $491 total
includes taxes & fees
Sep 2 - Sep 3
American Beech in Greenport - Petite King Room 7
Coastal Retreat With Saltwater Heated Pool, 5 Min To Beach, Fire Pit, 4 BDRM
Smart TV, fireplace

Coastal Retreat With Saltwater Heated Pool, 5 Min To Beach, Fire Pit, 4 BDRM

10.0 out of 10, Exceptional, (2)
"Just as we hoped"
The price is CA $1,254
CA $2,257 total
includes taxes & fees
Sep 1 - Sep 2
Coastal Retreat With Saltwater Heated Pool, 5 Min To Beach, Fire Pit, 4 BDRM
Private beach on a fenced in property sunset views
Terrace/patio

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (10)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
Private beach on a fenced in property sunset views
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Pool

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

9.2 out of 10, Wonderful, (9)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
The price is CA $908
CA $1,707 total
includes taxes & fees
Sep 28 - Sep 29
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Private kitchen

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

10.0 out of 10, Exceptional, (1)
"We were escaping NYC for the weekend and exploring real estate in the area. This house was absolutely beautiful and way bigger than we needed. Unfortunately it was rainy out and we really didn’t get to spend too much time in the house since we were driving around it looks like it has a beautiful property with a pool etc. so hopefully we can come back in the summer."
The price is CA $885
CA $1,460 total
includes taxes & fees
Sep 23 - Sep 24
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
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.
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Top Wainscott Woods Hotel Reviews

Find out more about Wainscott Woods

Find out more about Wainscott Woods

Wainscott Woods Vacation Homes information

Number of reviews
441
Accommodation
1754 Vacation Homes
Lowest Price
CA $304
Highest Price
CA $1,107

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