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

Cutchogue Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cutchogue vacation rentals

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $239
CA $430 total
includes taxes & fees
Nov 15 - Nov 16
Cliffside Resort Condominiums

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (66 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $414
CA $473 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort

3. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is CA $107
CA $639 total
includes taxes & fees
Oct 25 - Oct 26
Steps to the beach | Seabreeze Cottage #3

4. 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 CA $135
CA $357 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper

5. 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 CA $134
CA $352 total
includes taxes & fees
Nov 17 - Nov 18
Aqua Vista

6. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $134
CA $357 total
includes taxes & fees
Nov 3 - Nov 4
Harbor Heights

7. 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, (34 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 CA $205
CA $544 total
includes taxes & fees
Nov 2 - Nov 3
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

8. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is CA $204
CA $451 total
includes taxes & fees
Oct 21 - Oct 22
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

9. 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 CA $276
CA $630 total
includes taxes & fees
Nov 3 - Nov 4
Beach Block Hideaway

10. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $48
CA $564 total
includes taxes & fees
Oct 18 - Oct 19
Walk to Beach | Seabreeze Cottage #4

11. 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 CA $281
CA $433 total
includes taxes & fees
Oct 18 - Oct 19
American Beech in Greenport - Petite King Room 7

12. 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 CA $721
CA $1,763 total
includes taxes & fees
Oct 31 - Nov 1
North Fork Fall Escape—Vineyards, Apple Picking & Greenport

13. 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 CA $124
CA $1,626 total
includes taxes & fees
Oct 18 - Oct 19
Beachfront Jacuzzi All Year - Black Swan Home

14. 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 CA $158
CA $2,374 total
includes taxes & fees
Oct 28 - Oct 29
Jacuzzi year-round - Villa Luz Private Home

15. 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 CA $269
CA $887 total
includes taxes & fees
Oct 25 - Oct 26
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

16. 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 CA $704
CA $1,621 total
includes taxes & fees
Oct 18 - Oct 19
Amazing Southampton Home with Private Heated Pool

17. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is CA $318
CA $721 total
includes taxes & fees
Oct 19 - Oct 20
Charming Accommodations in the Hamptons

18. 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 CA $369
CA $814 total
includes taxes & fees
Nov 4 - Nov 5
Northfork Townhouse walk to all

19. 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 CA $762
CA $1,618 total
includes taxes & fees
Oct 18 - Oct 19
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

20. 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 CA $636
CA $1,548 total
includes taxes & fees
Oct 18 - Oct 19
Minutes from the beach, brand new 4 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cutchogue Hotel Reviews

Find out more about Cutchogue

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cutchogue. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Cutchogue?

Yes, you can find vacation rentals in Cutchogue close to 8 Hands Farm, or you can choose a more secluded option if you want a relaxing stay.

What are some of the best vacation rentals that Cutchogue has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental outside of Cutchogue offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Cutchogue?

With 37 Expedia vacation rentals, you're sure to find just the right place for your Cutchogue stay.

What’s there to see and do in Cutchogue?

Cutchogue Village Green and Fisherman Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Peconic Bay Winery and Bedell Cellars are other places worth a visit.

What’s a vacation rental in Cutchogue like?

Vacation rentals are private properties you can stay in for short or long periods in Cutchogue. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.