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

Cutchogue Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Cutchogue vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
$289 nightly
The price is $330
Nov 26 - Nov 27
Total with taxes and fees
Cliffside Resort Condominiums
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

2. 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
$429 nightly
The price is $454
Nov 15 - Nov 16
Total with taxes and fees
Steps to the beach | Seabreeze Cottage #3
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$194 nightly
The price is $221
Nov 15 - Nov 16
Total with taxes and fees
Harbor Heights
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

4. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
$423 nightly
The price is $448
Nov 16 - Nov 17
Total with taxes and fees
Cozy Cottage by the beach - Seabreeze #1
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
$203 nightly
The price is $232
Nov 30 - Dec 1
Total with taxes and fees
The SandPiper
A modern house with a deck, outdoor seating, and a fire pit.

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
$302 nightly
The price is $345
Nov 17 - Nov 18
Total with taxes and fees
North Fork Resort
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
$210 nightly
The price is $240
Nov 18 - Nov 19
Total with taxes and fees
Aqua Vista
A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

8. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
United States
Kelly V.
$414 nightly
The price is $473
Nov 23 - Nov 24
Total with taxes and fees
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
A residential property with a covered patio, outdoor seating, and a hot tub.

9. 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.
$1,085 nightly
The price is $1,143
Nov 13 - Nov 14
Total with taxes and fees
Jacuzzi year-round - Villa Luz Private Home
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

10. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$429 nightly
The price is $454
Nov 17 - Nov 18
Total with taxes and fees
Walk to Beach | Seabreeze Cottage #4
A beach with people relaxing, a pier extending into the water, and a clear sky.

11. 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.
$305 nightly
The price is $348
Nov 15 - Nov 16
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

12. 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, (7 reviews)
"This was a great property. Very convenient to where we like to visit. It really had everything we needed for a great weeks stay."
United States
Sherri K.
$283 nightly
The price is $323
Dec 1 - Dec 2
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
An outdoor dining area with hanging lights, palm trees, and a bar.

13. 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.
$252 nightly
The price is $288
Nov 15 - Nov 16
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

14. 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.
$375 nightly
The price is $428
Nov 15 - Nov 16
Total with taxes and fees
Beach Block Hideaway
A house with a sliding glass door, a white door, and a small porch with potted plants.

15. 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.
$532 nightly
The price is $608
Nov 13 - Nov 14
Total with taxes and fees
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern building with large windows overlooking a beach.

16. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
$1,178 nightly
The price is $1,243
Nov 15 - Nov 16
Total with taxes and fees
Beachfront Jacuzzi All Year - Black Swan Home
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

17. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$434 nightly
The price is $496
Nov 16 - Nov 17
Total with taxes and fees
Charming Accommodations in the Hamptons
A wooden interior with a staircase, a blue sofa, and a fireplace.

18. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"House has so much character, I rent 7-8 weeks per year and every home is different.This house is the most organized I have ever been in but also the most character.Every room brings you to different place, the furniture is beautiful. Home is spacious.Grounds are larger than most in the Hamptons. Pool is spectacular!"
United States
Frank T.
$1,309 nightly
The price is $1,384
Dec 1 - Dec 2
Total with taxes and fees
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Terrace/patio

19. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$354 nightly
The price is $405
Nov 15 - Nov 16
Total with taxes and fees
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
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.

20. 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.
$469 nightly
The price is $535
Nov 16 - Nov 17
Total with taxes and fees
Renovated Townhouse walk to all
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

Spark by Hilton Guilford

Spark by Hilton Guilford

10/10 Excellent
"This was my first time staying and will absolutely be coming back! The rooms were clean and lovely. Breakfast was a perfect start to our early mornings. And the staff was so nice and welcoming!"
Bryauna 2-night trip
Posted 1 hour ago
Spark by Hilton Guilford

Find out more about Cutchogue

Everything you need to know about Cutchogue vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cutchogue vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cutchogue vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cutchogue vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cutchogue. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cutchogue in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $253 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cutchogue rentals

At Expedia, we put the best Cutchogue vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cutchogue rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cutchogue vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cutchogue. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.