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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Cutchogue vacation homes

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

1. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, 10, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥29,954
￥64,232 total
includes taxes & fees
Sep 15 - Sep 16
Beach Block Hideaway
A beach with people relaxing, a pier extending into the water, and a clear sky.

2. 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, 31, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥26,959
￥62,389 total
includes taxes & fees
Sep 15 - Sep 16
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, 45, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,273
￥47,036 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, 52, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥29,954
￥57,742 total
includes taxes & fees
Sep 28 - Sep 29
The SandPiper
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

5. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, 26, (26 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥17,204
￥257,843 total
includes taxes & fees
Sep 21 - Sep 22
Villa Luz Family Home w/ heated pool & jacuzzi
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, 6, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is ￥36,713
￥54,934 total
includes taxes & fees
Sep 16 - Sep 17
American Beech in Greenport - Petite King Room 7
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

7. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, 43, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is ￥69,125
￥150,403 total
includes taxes & fees
Sep 15 - Sep 16
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern building with large windows overlooking a beach.

8. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.4 out of 10, 19, (19 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 ￥33,487
￥200,532 total
includes taxes & fees
Sep 27 - Sep 28
Black Swan Beachfront Home with Jacuzzi year round
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

9. 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, 1, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is ￥43,779
￥90,208 total
includes taxes & fees
Sep 22 - Sep 23
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A dining area with a round table, six chairs, and a chandelier.

10. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, 7, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ￥13,518
￥198,265 total
includes taxes & fees
Sep 15 - Sep 16
BlackBerry Private home with jacuzzi yearlong
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, 1, (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 ￥87,097
￥171,114 total
includes taxes & fees
Sep 15 - Sep 16
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A spacious living room with a stone fireplace, wooden beams, a white sofa, and a cowhide rug.

12. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, 5, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is ￥115,208
￥220,254 total
includes taxes & fees
Sep 15 - Sep 16
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

13. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, 17, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥25,438
￥72,441 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Cottage, 5 min walk to water & town
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

14. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, 58, (58 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
The price is ￥110,599
￥204,458 total
includes taxes & fees
Sep 15 - Sep 16
Work and Play Special! Extended Stay Discount
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.

15. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, 14, (14 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is ￥55,991
￥109,248 total
includes taxes & fees
Sep 17 - Sep 18
Renovated Townhouse walk to all
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

16. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
The price is ￥200,461
￥293,962 total
includes taxes & fees
Sep 15 - Sep 16
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

17. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, 2, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥25,008
￥82,561 total
includes taxes & fees
Sep 15 - Sep 16
Beachside Bliss w/ Game Room, Gym & Golf Green
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, 13, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥150,000
￥227,186 total
includes taxes & fees
Sep 17 - Sep 18
Beachfront Greenport Villa
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

19. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, 2, (2 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
The price is ￥66,360
￥182,727 total
includes taxes & fees
Sep 16 - Sep 17
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

20. 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, 11, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ￥76,728
￥158,387 total
includes taxes & fees
Sep 17 - Sep 18
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

8/10 Good
"Everything about my stay was great besides finding parking. There is no onsite parking"
Greg 1-night trip
Posted 2 hours ago
Hampton Bays Hotel on Main

Find out more about Cutchogue

Cutchogue Vacation Homes information

Number of reviews
5,137
Accommodation
1277 Vacation Homes
Lowest Price
￥12,189
Highest Price
￥116,659