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 £189
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 £189
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
A wooden pathway leading to a beach with scattered rocks and greenery.

4. 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 £340
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
An outdoor dining area with hanging lights, palm trees, and a bar.

5. 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
25 Oct - 26 Oct
American Beech in Greenport - Petite King Room 7
A wooden interior with a staircase, a blue sofa, and a fireplace.

6. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is £1,075
includes taxes & fees
17 Nov - 18 Nov
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
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 £944
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 £1,247
includes taxes & fees
28 Oct - 29 Oct
Jacuzzi year-round - Villa Luz Private Home
A modern building with large windows overlooking a beach.

9. 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
29 Oct - 30 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

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 £857
includes taxes & fees
21 Oct - 22 Oct
Amazing Southampton Home with Private Heated Pool
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

11. 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 £469
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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 £423
includes taxes & fees
4 Nov - 5 Nov
Northfork Townhouse walk to all
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

13. 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 £873
includes taxes & fees
21 Oct - 22 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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.

14. 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 £440
includes taxes & fees
21 Oct - 22 Oct
Renovated Townhouse walk to all
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

15. 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
22 Oct - 23 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

16. 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
29 Oct - 30 Oct
Minutes from the beach, brand new 4 bedroom
A wooden house with a front porch, white railings, and a double door.

17. 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 £2,150
includes taxes & fees
29 Oct - 30 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

18. 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 £763
includes taxes & fees
18 Nov - 19 Nov
Beachfront Greenport Villa
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

19. 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 £428
includes taxes & fees
25 Oct - 26 Oct
Immaculate Waterfront 2 bedroom!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

20. 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 £439
includes taxes & fees
8 Nov - 9 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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

Sag Harbor Inn

Sag Harbor Inn

10/10 Excellent
"The hotel was beautiful. The room was very spacious and comfortable. The continental breakfast offered many choices, and they had coffee, tea and hot chocolate available 24 hours a day."
Francine 2-night trip
Posted 3 hours ago
Sag Harbor Inn

Find out more about Cutchogue

Cutchogue Holiday Homes information

Number of reviews
290
Accommodation
1242 Holiday Homes
Lowest Price
£189
Highest Price
£2,150