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

Holiday Homes in Cutchogue

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 €205
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, (51 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is €216
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A wooden interior with a staircase, a blue sofa, and a fireplace.

3. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is €1,133
includes taxes & fees
11 Nov - 12 Nov
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
A beach with people relaxing, a pier extending into the water, and a clear sky.

4. 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 great stay!! "
United States
Callie E.
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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 €372
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
An outdoor dining area with hanging lights, palm trees, and a bar.

6. 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 €262
includes taxes & fees
3 Nov - 4 Nov
American Beech in Greenport - Petite King Room 7
A hot tub with a checkered roof structure and surrounding greenery.

7. 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 €1,557
includes taxes & fees
7 Nov - 8 Nov
Jacuzzi year-round - Villa Luz Private Home
A house with a covered outdoor seating area, a well-maintained lawn, and a sunset in the background.

8. 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)
"Great home overall. Backyard was huge! Pool and seating options were was amazing!"
United States
Vanessa S.
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
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 €475
includes taxes & fees
2 Nov - 3 Nov
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A modern building with large windows overlooking a beach.

10. 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 €1,139
includes taxes & fees
2 Nov - 3 Nov
Beachfront Jacuzzi All Year - Black Swan Home
A modern dining area with a wooden table, white chairs, and a chandelier.

11. 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.
Northfork Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

12. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
Beachfront Greenport Villa
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.

13. 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.
Renovated Townhouse walk to all
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

14. 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 €975
includes taxes & fees
3 Nov - 4 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A wooden house with a front porch, white railings, and a double door.

15. 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 €2,443
includes taxes & fees
3 Nov - 4 Nov
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
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 €907
includes taxes & fees
2 Nov - 3 Nov
Minutes from the beach, brand new 4 bedroom
A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

17. 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 €503
includes taxes & fees
8 Nov - 9 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

18. 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 €487
includes taxes & fees
2 Nov - 3 Nov
Immaculate Waterfront 2 bedroom!
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

19. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is €1,675
includes taxes & fees
7 Nov - 8 Nov
Newly Renovated Pristine Southampton Colonial
A modern living room with a sofa, armchairs, a coffee table, and a TV.

20. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is €998
includes taxes & fees
30 Nov - 1 Dec
Minutes from the beach, brand new 3 bedroom
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cutchogue Hotel Reviews

Seven Beach Lane

Seven Beach Lane

10/10 Excellent
"was great"
Daniel 1-night trip
Posted 2 hours ago
Seven Beach Lane

Find out more about Cutchogue

Cutchogue Holiday Homes information

Number of reviews
283
Accommodation
1242 Holiday Homes
Lowest Price
€205
Highest Price
€2,443