A lighthouse on a rocky outcrop with a grassy area and buildings nearby.

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Our top choices for Montauk vacation homes

1. 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 Village
Stonington
9.8 out of 10, Exceptional, (193 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is ¥15,817
¥39,279 total
includes taxes & fees
Nov 17 - Nov 18
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

2. 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 parks
Waterford
10.0 out of 10, Exceptional, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ¥27,881
¥70,880 total
includes taxes & fees
Nov 30 - Dec 1
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is ¥15,178
¥37,421 total
includes taxes & fees
Nov 30 - Dec 1
The SandPiper

4. 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 ¥116,616
¥217,929 total
includes taxes & fees
Dec 1 - Dec 2
Spacious house in East Hampton with heated pool + WFH

5. 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, (182 reviews)
"Great location "
United States
Brian S.
The price is ¥26,538
¥54,781 total
includes taxes & fees
Dec 9 - Dec 10
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

6. Groton Long Point Cottage with AC - 10 Min to Mystic!

Groton Long Point Cottage with AC - 10 Min to Mystic!
Groton
The price is ¥35,948
¥83,815 total
includes taxes & fees
Nov 30 - Dec 1
Groton Long Point Cottage with AC - 10 Min to Mystic!

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is ¥15,178
¥38,335 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Vista

8. 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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ¥20,850
¥55,582 total
includes taxes & fees
Nov 15 - Nov 16
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

9. 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 ¥31,794
¥46,367 total
includes taxes & fees
Nov 15 - Nov 16
American Beech in Greenport - Petite King Room 7

10. Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street
East Hampton
The price is ¥128,263
¥187,613 total
includes taxes & fees
Nov 14 - Nov 15
Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

11. Beach Block Hideaway

Beach Block Hideaway
Pipes 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."
United States
Teresa C.
The price is ¥31,155
¥68,450 total
includes taxes & fees
Nov 15 - Nov 16
Beach Block Hideaway

12. The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
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. "
United States
Bethany M.
The price is ¥29,468
¥68,864 total
includes taxes & fees
Nov 16 - Nov 17
The Blue Anchor House · walk Mystic-Train/Aquarium

13. 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, (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!"
United States
Suzanne B.
The price is ¥137,466
¥324,988 total
includes taxes & fees
Nov 18 - Nov 19
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

14. 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 "
United States
dolly o.
The price is ¥37,349
¥104,331 total
includes taxes & fees
Nov 16 - Nov 17
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

15. 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"
United States
Katie B.
The price is ¥45,534
¥89,263 total
includes taxes & fees
Nov 15 - Nov 16
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

16. Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT

Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Groton
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."
United States
Benjamin G.
The price is ¥61,336
¥126,672 total
includes taxes & fees
Nov 15 - Nov 16
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT

17. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (196 reviews)
"A wonderful stay "
United States
Gina P.
The price is ¥47,931
¥82,601 total
includes taxes & fees
Dec 9 - Dec 10
Charming Historic House in Downtown Mystic

18. 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 ¥46,362
¥97,145 total
includes taxes & fees
Nov 14 - Nov 15
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

19. The Mystic Harbor House · walk downtown Mystic · train · aquarium

The Mystic Harbor House · walk downtown Mystic · train · aquarium
Stonington
9.8 out of 10, Exceptional, (11 reviews)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
United States
David C.
The price is ¥42,387
¥84,780 total
includes taxes & fees
Nov 15 - Nov 16
The Mystic Harbor House · walk downtown Mystic · train · aquarium

20. Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY

Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
West Mystic
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place for family fun!"
United States
nancy m.
The price is ¥63,748
¥78,742 total
includes taxes & fees
Nov 15 - Nov 16
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
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 Montauk Hotel Reviews

Find out more about Montauk

Montauk Vacation Homes information

Number of reviews
1,024
Accommodation
70 Vacation Homes
Lowest Price
¥37,421
Highest Price
¥324,988