A coastal sunset with a beach, ocean waves, and a road leading to a distant town.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Amagansett vacation homes

Exterior

1. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is AED 1,190
AED 2,370 total
includes taxes & fees
27 Sep - 28 Sep
Unit 1311: Cottage | Garden View | Deuce
TV

2. Unit 511: Cottage | Ocean View | Nautilus

Unit 511: Cottage | Ocean View | Nautilus
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
The price is AED 1,781
AED 3,159 total
includes taxes & fees
26 Sep - 27 Sep
Unit 511: Cottage | Ocean View | Nautilus
Dining

3. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
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 AED 415
AED 4,854 total
includes taxes & fees
27 Sep - 28 Sep
Year round Jacuzzi - Blackberry Home
Pool

4. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is AED 881
AED 3,482 total
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
Private kitchen

5. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is AED 1,653
AED 3,932 total
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH
Property grounds

6. 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 AED 1,221
AED 2,386 total
includes taxes & fees
11 Oct - 12 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Sun loungers, beach towels

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (46 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 533
AED 1,133 total
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
Sun loungers, beach towels

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AED 533
AED 1,175 total
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
Sun loungers, beach towels

9. 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 AED 645
AED 1,563 total
includes taxes & fees
27 Sep - 28 Sep
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Coffee/tea maker, fridge, microwave, oven

10. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (33 reviews)
"Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend! "
United States
Leigh E.
The price is AED 3,891
AED 8,339 total
includes taxes & fees
4 Oct - 5 Oct
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Outdoor pool, a heated pool

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, 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 AED 2,083
AED 3,907 total
includes taxes & fees
26 Sep - 27 Sep
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Terrace/patio

12. 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 AED 731
AED 1,125 total
includes taxes & fees
4 Oct - 5 Oct
American Beech in Greenport - Petite King Room 7
Beach

13. 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 AED 900
AED 1,775 total
includes taxes & fees
4 Oct - 5 Oct
Beach Block Hideaway
Interior

14. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is AED 5,620
AED 8,175 total
includes taxes & fees
26 Sep - 27 Sep
Lovely & Spacious Sag Harbor escape with heated pool
Coffee/tea maker, fridge, microwave, oven

15. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 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 AED 2,645
AED 4,889 total
includes taxes & fees
27 Sep - 28 Sep
Work and Play Special! Extended Stay Discount
Private kitchen

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 AED 6,883
AED 9,820 total
includes taxes & fees
28 Sep - 29 Sep
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sun loungers, beach towels

17. Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower

Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
Culloden Shores
8.6 out of 10, Excellent, (4 reviews)
"Definitely more space than expected, and super close to everything in Montauk. Planning on coming back next year!"
United States
Nick M.
The price is AED 1,511
AED 3,699 total
includes taxes & fees
19 Oct - 20 Oct
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
Terrace/patio

18. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach
Menantic Creek
9.8 out of 10, Exceptional, (9 reviews)
"Property great. Beautiful home with great amenities"
United States
Harry K.
The price is AED 2,446
AED 4,300 total
includes taxes & fees
5 Oct - 6 Oct
Huge Island Getaway Pool Hot Tub Walk To Beach
Smart TV, fireplace

19. 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 AED 1,273
AED 2,524 total
includes taxes & fees
20 Oct - 21 Oct
Renovated Townhouse walk to all
Interior

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, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is AED 1,653
AED 3,550 total
includes taxes & fees
21 Oct - 22 Oct
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 Amagansett Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"We stayed in the ocean front room. The room and view were beautiful. We had dinner at GIGIs. The food was good. The menu selection Was limited for us because we do not eat fish. The negative with Gurneys is the rooms are not connected to the main building. They do provide a car service to pick you up. I feel this limits you. We would have gone down for a drink but it seemed too involved to get there. This resort is not for seniors ."
salvatore 2-night trip
Posted 2 hours ago
Gurney's Montauk Resort & Seawater Spa