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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Montauk vacation homes

A sandy beach path with wooden fencing leading to the ocean.

1. 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 1,285
AED 3,369 total
includes taxes & fees
21 Oct - 22 Oct
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

2. 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 1,109
AED 2,260 total
includes taxes & fees
12 Oct - 13 Oct
Unit 1311: Cottage | Garden View | Deuce
A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton 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
12 Oct - 13 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

4. 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.
Unit 511: Cottage | Ocean View | Nautilus
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

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 3,907 total
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH
A two-story house with a porch and a wooden picnic table in the front yard.

6. 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, (191 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is AED 371
AED 956 total
includes taxes & fees
4 Nov - 5 Nov
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A living room with a fireplace, a grey armchair, and a large window.

7. 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 AED 724
AED 1,765 total
includes taxes & fees
8 Nov - 9 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AED 349
AED 906 total
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

9. 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, (178 reviews)
"Great location "
United States
Brian S.
The price is AED 602
AED 1,250 total
includes taxes & fees
4 Nov - 5 Nov
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A kitchen with a central island, white cabinetry, and a brick accent wall.

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, (34 reviews)
"Loved it! Thank you for having us."
United States
Vera P.
The price is AED 4,283
AED 8,846 total
includes taxes & fees
8 Nov - 9 Nov
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

11. 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 1,047
AED 2,157 total
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
An outdoor dining area with hanging lights, palm trees, and a bar.

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
1 Nov - 2 Nov
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

13. 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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 533
AED 1,414 total
includes taxes & fees
1 Nov - 2 Nov
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.

14. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 533
AED 1,175 total
includes taxes & fees
12 Oct - 13 Oct
Aqua Vista
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

15. 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 AED 715
AED 1,707 total
includes taxes & fees
3 Nov - 4 Nov
The Blue Anchor House · walk Mystic-Train/Aquarium
A wooden pathway leading to a beach with scattered rocks and greenery.

16. 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 AED 716
AED 1,653 total
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

17. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (193 reviews)
"A wonderful stay "
United States
Gina P.
The price is AED 859
AED 1,587 total
includes taxes & fees
19 Oct - 20 Oct
Charming Historic House in Downtown Mystic
A modern living room with a fireplace, a large window with a view of a beach, and a 'Welcome to the Farm' sign.

18. 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, (143 reviews)
"Loved the woods next to it. The stained glass were very cool"
United States
Kate R.
The price is AED 1,410
AED 2,912 total
includes taxes & fees
18 Oct - 19 Oct
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
A covered patio with a wooden table and white chairs, large windows, and a view of a deck and trees.

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 AED 951
AED 2,011 total
includes taxes & fees
3 Nov - 4 Nov
The Mystic Harbor House · walk downtown Mystic · train · aquarium
A white house with green shutters, a red door, and a flag.

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 "
United States
dolly o.
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
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

The Surf Club

The Surf Club

10/10 Excellent
"Staff are nice"
na 1-night trip
Posted 1 hour ago
The Surf Club

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