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Search Vacation Homes in Wainscott Woods

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Wainscott Woods vacation homes

Private kitchen
Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
$1,702 nightly
The price is $1,945
Dec 14 - Dec 15
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,353 nightly
The price is $7,259
Dec 15 - Dec 16
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$771 nightly
The price is $881
Dec 16 - Dec 17
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

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

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
$5,630 nightly
The price is $6,432
Dec 17 - Dec 18
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$242 nightly
The price is $277
Dec 14 - Dec 15
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
$5,589 nightly
The price is $6,385
Dec 15 - Dec 16
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all
Greenport
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
$583 nightly
The price is $666
Dec 14 - Dec 15
Total with taxes and fees
Charming Northfork Townhouse- walk to all
A heated pool
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

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

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15)
"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"
United States
William H.
$1,504 nightly
The price is $1,593
Jan 5 - Jan 6, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Fridge, oven, stovetop, dishwasher
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Upscale Hamptons Home: 1 Mi to Sammys Beach!

Upscale Hamptons Home: 1 Mi to Sammys Beach!
East Hampton
9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!
Terrace/patio
Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$547 nightly
The price is $625
Dec 14 - Dec 15
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Dining
Designer East Hampton Farmhouse

Designer East Hampton Farmhouse

Designer East Hampton Farmhouse
East Hampton North
$1,057 nightly
The price is $1,127
Jan 2 - Jan 3, 2026
Total with taxes and fees
Designer East Hampton Farmhouse
Fridge, microwave, oven, stovetop
Serene East Hampton Escape

Serene East Hampton Escape

Serene East Hampton Escape
2.0 star property
East Hampton North
$1,001 nightly
The price is $1,065
Jan 2 - Jan 3, 2026
Total with taxes and fees
Serene East Hampton Escape
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated
Greenport
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$617 nightly
The price is $705
Dec 14 - Dec 15
Total with taxes and fees
Northfork Townhouse- walk to all/ newly renovated
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Dec 15 - Dec 16
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom
Interior
Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
$800 nightly
The price is $914
Dec 14 - Dec 15
Total with taxes and fees
Cozy Hamptons Escape 3BR Minutes From Beach!
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.0 out of 10, Wonderful, (10)
"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!"
United States
Panagiota K.
$832 nightly
The price is $950
Dec 16 - Dec 17
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Living area
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi

4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi
East Hampton
$1,485 nightly
The price is $1,697
Dec 31 - Jan 1, 2026
Total with taxes and fees
4-bedroom 3-bathroom house in fabulous East Hampton with AC, WiFi
Dining
Tranquil 4-bedroom house with AC in East Quogue. Covered patio.

Tranquil 4-bedroom house with AC in East Quogue. Covered patio.

Tranquil 4-bedroom house with AC in East Quogue. Covered patio.
East Quogue
$1,478 nightly
The price is $1,689
Dec 17 - Dec 18
Total with taxes and fees
Tranquil 4-bedroom house with AC in East Quogue. Covered patio.
Property grounds
American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
$300 nightly
The price is $343
Dec 14 - Dec 15
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
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

Montauk Manor

Montauk Manor

10/10 Excellent
"Everything was perfect. Only disappointment was not being able to get a couple’s massage or even at the same time(understandable as only one person working in the spa) and was looking forward to sitting bybthe indoor pool to read and relax but they do not have chairs only benches. Jacuzzi kind of small also. Overall we really enjoyed our stay!! "
Donna 2-night trip
Posted 1 day ago
Montauk Manor

Find out more about Wainscott Woods

Wainscott Woods Vacation Homes information

Number of reviews
71
Accommodation
1575 Vacation Homes
Lowest Price
$277
Highest Price
$7,259

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