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

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, 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 NZ$717
includes taxes & fees
15 Sept - 16 Sept
Beach Block Hideaway
A modern building with large windows overlooking a beach.

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 NZ$2,060
includes taxes & fees
13 Sept - 14 Sept
Black Swan Beachfront Home with Jacuzzi year round
A beach with people relaxing, a pier extending into the water, and a clear sky.

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 NZ$730
includes taxes & fees
16 Sept - 17 Sept
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.

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 NZ$538
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
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, (52 reviews)
"access"
United States
Timothy
The price is NZ$648
includes taxes & fees
28 Sept - 29 Sept
The SandPiper
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 NZ$603
includes taxes & fees
23 Sept - 24 Sept
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, 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 NZ$1,639
includes taxes & fees
27 Sept - 28 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

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 NZ$2,995
includes taxes & fees
23 Sept - 24 Sept
Villa Luz Family Home w/ heated pool & jacuzzi
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, 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 NZ$967
includes taxes & fees
22 Sept - 23 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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 NZ$2,145
includes taxes & fees
16 Sept - 17 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A dining area with a round table, six chairs, and a chandelier.

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 NZ$2,190
includes taxes & fees
13 Sept - 14 Sept
BlackBerry Private home with jacuzzi yearlong
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, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is NZ$2,381
includes taxes & fees
13 Sept - 14 Sept
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

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 NZ$2,187
includes taxes & fees
16 Sept - 17 Sept
Work and Play Special! Extended Stay Discount
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

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 NZ$814
includes taxes & fees
13 Sept - 14 Sept
Adorable Cottage, 5 min walk to water & town
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, 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.
Renovated Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

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 NZ$2,567
includes taxes & fees
17 Sept - 18 Sept
Beachfront Greenport Villa
A modern dining area with a wooden table, white chairs, and a chandelier.

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 NZ$1,426
includes taxes & fees
13 Sept - 14 Sept
Northfork Townhouse walk to all
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

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 NZ$3,203
includes taxes & fees
13 Sept - 14 Sept
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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 NZ$1,737
includes taxes & fees
13 Sept - 14 Sept
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

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 NZ$2,521
includes taxes & fees
22 Sept - 23 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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Deverian actualizar las tv’s"
Maria 1-night trip
Posted 16 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Cutchogue

Cutchogue Holiday Homes information

Number of reviews
342
Accommodation
1258 Holiday Homes
Lowest Price
NZ$538
Highest Price
NZ$2,995