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Our top choices for Montauk holiday homes
1. Year round Jacuzzi - Blackberry East Hampton Home
Year round Jacuzzi - Blackberry East Hampton HomeEast 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 "
Suzanne R.
The price is NZ$2,423
includes taxes & fees
10 Nov - 11 Nov
2. Serene, chic East Hampton home - minutes to beaches, Main St., and so much more
Serene, chic East Hampton home - minutes to beaches, Main St., and so much moreEast Hampton
The price is NZ$2,091
includes taxes & fees
10 Nov - 11 Nov
3. Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington VillageStonington
9.8 out of 10, Exceptional, (193 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
Jaime M.
The price is NZ$444
includes taxes & fees
10 Nov - 11 Nov
4. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parksWaterford
10.0 out of 10, Exceptional, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
Elaine A.
The price is NZ$799
includes taxes & fees
11 Nov - 12 Nov
5. Spacious house in East Hampton with heated pool + WFH
Spacious house in East Hampton with heated pool + WFHEast Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
ANGELA S.
The price is NZ$2,413
includes taxes & fees
1 Dec - 2 Dec
6. Luxury Village Rental in the Heart of Sag Harbor
Luxury Village Rental in the Heart of Sag HarborSag Harbor
The price is NZ$1,476
includes taxes & fees
10 Nov - 11 Nov
7. Groton Long Point Cottage with AC - 10 Min to Mystic!
Groton Long Point Cottage with AC - 10 Min to Mystic!Groton
The price is NZ$937
includes taxes & fees
30 Nov - 1 Dec
8. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great location and nice spot."
Kerri L.
The price is NZ$429
includes taxes & fees
18 Nov - 19 Nov
9. The SandPiper
The SandPiperPipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
Manuela C.
The price is NZ$411
includes taxes & fees
10 Nov - 11 Nov
10. !! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
Suzanne B.
The price is NZ$3,446
includes taxes & fees
19 Nov - 20 Nov
11. Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Charming 1845 Home in the Heart of Mystic – Walk to Everything!Mystic River Historic District
9.8 out of 10, Exceptional, (181 reviews)
"Great location "
Brian S.
The price is NZ$471
includes taxes & fees
11 Nov - 12 Nov
12. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + OfficePipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
Callie E.
The price is NZ$626
includes taxes & fees
10 Nov - 11 Nov
13. American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
Paul F.
The price is NZ$521
includes taxes & fees
10 Nov - 11 Nov
14. The Blue Anchor House · walk Mystic-Train/Aquarium
The Blue Anchor House · walk Mystic-Train/AquariumStonington
10.0 out of 10, Exceptional, (10 reviews)
"The house was clean, spacious and the location was perfect for all of our needs. Host was responsive when we reached out. Would definitely stay here again, and plan to in the future. "
Bethany M.
The price is NZ$737
includes taxes & fees
11 Nov - 12 Nov
15. Groton Home < 1 Mi to Beach on Long Island Sound!
Groton Home < 1 Mi to Beach on Long Island Sound!Groton
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful home, so much space. Kitchen was wonderful and had anything you needed to serve a meal. Wonderful covered deck out back, overlooking golf course to the Thames river. Owners very responsive. Will go back."
Lois S.
The price is NZ$1,386
includes taxes & fees
22 Nov - 23 Nov
16. 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, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
Katie B.
The price is NZ$1,002
includes taxes & fees
15 Nov - 16 Nov
17. Beach Block Hideaway
Beach Block HideawayPipes 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."
Teresa C.
The price is NZ$756
includes taxes & fees
11 Nov - 12 Nov
18. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Designer Sag Harbor Home w/ Pool + Fire Pit + YardSag 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!"
maria m.
The price is NZ$1,976
includes taxes & fees
10 Nov - 11 Nov
19. Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CTGroton
10.0 out of 10, Exceptional, (146 reviews)
"Lovely property and super easy communication and check-in/check-out process with the host. Would definitely book again."
Benjamin G.
The price is NZ$1,407
includes taxes & fees
10 Nov - 11 Nov
20. Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!Mystic River Historic District
10.0 out of 10, Exceptional, (97 reviews)
"Great location responsive hosts fully stocked cozy accommodations "
dolly o.
The price is NZ$1,224
includes taxes & fees
10 Nov - 11 Nov
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.
Learn more about Montauk
The lighthouse stands sentinel at the island's edge, where surfers catch waves and fishermen cast lines at sunrise. Hike the bluffs for dramatic Atlantic views, then sample fresh seafood at dockside restaurants where locals gather after sunset.
