A coastal landscape with a sandy beach, calm waters, and a clear sky.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Cutchogue holiday homes

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is £192
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £192
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is £281
includes taxes & fees
2 Nov - 3 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

4. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is £231
includes taxes & fees
20 Oct - 21 Oct
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is £337
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A modern building with large windows overlooking a beach.

6. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is £908
includes taxes & fees
27 Oct - 28 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A rocky beach with clear water and a forested hillside in the background.

7. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is £937
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

8. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £1,269
includes taxes & fees
29 Oct - 30 Oct
Jacuzzi year-round - Villa Luz Private Home
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is £468
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A basketball hoop in a park with a metal frame and a backboard, surrounded by trees and grass.

10. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is £878
includes taxes & fees
20 Oct - 21 Oct
Amazing Southampton Home with Private Heated Pool
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

11. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is £872
includes taxes & fees
20 Oct - 21 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern dining area with a wooden table, white chairs, and a chandelier.

12. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 reviews)
"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.
The price is £409
includes taxes & fees
20 Oct - 21 Oct
Northfork Townhouse walk to all
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

13. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is £827
includes taxes & fees
20 Oct - 21 Oct
Minutes from the beach, brand new 4 bedroom
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

14. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is £758
includes taxes & fees
10 Nov - 11 Nov
Beachfront Greenport Villa
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

15. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is £430
includes taxes & fees
20 Oct - 21 Oct
Immaculate Waterfront 2 bedroom!
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

16. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
The price is £726
includes taxes & fees
20 Oct - 21 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

17. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is £443
includes taxes & fees
20 Oct - 21 Oct
Renovated Townhouse walk to all
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

18. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is £438
includes taxes & fees
3 Nov - 4 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A wooden house with a front porch, white railings, and a double door.

19. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is £2,126
includes taxes & fees
20 Oct - 21 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

20. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is £258
includes taxes & fees
20 Oct - 21 Oct
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 Cutchogue Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Property and room was incredible. However, didn’t like the restaurant food. It was lacking flavor and the dessert choices weren’t good. Lastly, the pillows weren’t the best."
Delise 2-night trip
Posted 13 hours ago
The Hampton Maid

Find out more about Cutchogue

Cutchogue Holiday Homes information

Number of reviews
291
Accommodation
1242 Holiday Homes
Lowest Price
£192
Highest Price
£2,126