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

Holiday Homes in Cutchogue

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Cutchogue holiday homes

Beach

1. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (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 AU$572
includes taxes & fees
15 Sept - 16 Sept
Beach Block Hideaway
Terrace/patio

2. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.4 out of 10, Exceptional, (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 AU$1,608
includes taxes & fees
13 Sept - 14 Sept
Black Swan Beachfront Home with Jacuzzi year round
Beach

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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$581
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Beach

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$451
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
Beach

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"access"
United States
Timothy
The price is AU$524
includes taxes & fees
28 Sept - 29 Sept
The SandPiper
Terrace/patio

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 AU$487
includes taxes & fees
22 Sept - 23 Sept
American Beech in Greenport - Petite King Room 7
Pool

7. 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)
"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 AU$1,344
includes taxes & fees
15 Sept - 16 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
Property grounds

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

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
The price is AU$2,253
includes taxes & fees
23 Sept - 24 Sept
Villa Luz Family Home w/ heated pool & jacuzzi
Property grounds

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, Exceptional, (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 AU$802
includes taxes & fees
22 Sept - 23 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Pool

10. 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 AU$1,679
includes taxes & fees
16 Sept - 17 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Dining

11. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (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 AU$1,806
includes taxes & fees
13 Sept - 14 Sept
BlackBerry Private home with jacuzzi yearlong
Interior

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, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is AU$1,964
includes taxes & fees
13 Sept - 14 Sept
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Private kitchen

13. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (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 AU$1,792
includes taxes & fees
22 Sept - 23 Sept
Work and Play Special! Extended Stay Discount
Interior

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AU$649
includes taxes & fees
13 Sept - 14 Sept
Adorable Cottage, 5 min walk to water & town
Living area

15. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (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 AU$1,001
includes taxes & fees
17 Sept - 18 Sept
Renovated Townhouse walk to all
Property grounds

16. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is AU$2,120
includes taxes & fees
17 Sept - 18 Sept
Beachfront Greenport Villa
Dining

17. 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 AU$1,161
includes taxes & fees
13 Sept - 14 Sept
Northfork Townhouse walk to all
Private kitchen

18. 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 AU$2,643
includes taxes & fees
13 Sept - 14 Sept
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Interior

19. 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 AU$1,416
includes taxes & fees
13 Sept - 14 Sept
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Living area

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 AU$2,080
includes taxes & fees
15 Sept - 16 Sept
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.
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Top Cutchogue Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
Michael 1-night trip
Posted less than an hour ago
Water's Edge Resort & Spa

Find out more about Cutchogue

Cutchogue Holiday Homes information

Number of reviews
342
Accommodation
1296 Holiday Homes
Lowest Price
AU$451
Highest Price
AU$2,253