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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 1,488
AED 3,483 total
includes taxes & fees
26 Oct - 27 Oct
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
A dining area with a round table, six chairs, and a chandelier.

2. 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 518
AED 4,699 total
includes taxes & fees
4 Oct - 5 Oct
Year round Jacuzzi - Blackberry Home
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

3. 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 2,236 total
includes taxes & fees
29 Sep - 30 Sep
Unit 1311: Cottage | Garden View | Deuce
A rectangular swimming pool with a pebble border and a fire feature in the center.

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
10.0 out of 10, Exceptional, (1 review)
The price is AED 881
AED 3,263 total
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
A two-story house with a porch and a wooden picnic table in the front yard.

5. 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, (190 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is AED 404
AED 960 total
includes taxes & fees
29 Sep - 30 Sep
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

6. 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 3,638 total
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

7. 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 2,178
AED 3,514 total
includes taxes & fees
5 Oct - 6 Oct
Unit 511: Cottage | Ocean View | Nautilus
A living room with a fireplace, a grey armchair, and a large window.

8. 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 620
AED 1,602 total
includes taxes & fees
30 Sep - 1 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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 469
AED 1,031 total
includes taxes & fees
30 Sep - 1 Oct
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A beach with people relaxing, a pier extending into the water, and a clear sky.

10. 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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 645
AED 1,462 total
includes taxes & fees
12 Oct - 13 Oct
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

11. 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 1,112 total
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (47 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 533
AED 1,112 total
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

13. 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 710
AED 1,617 total
includes taxes & fees
5 Oct - 6 Oct
The Blue Anchor House · walk Mystic-Train/Aquarium
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

14. 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 2,256 total
includes taxes & fees
13 Oct - 14 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A two-story house with a front porch, a black door, and a mailbox.

15. 3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (33 reviews)
"We will be back! great, responsive owners, phenomenal property and location! Go get breakfast at The Eatery down the road, it’s amazing!!"
United States
Travis C.
The price is AED 1,102
AED 2,408 total
includes taxes & fees
29 Sep - 30 Sep
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
An outdoor dining area with hanging lights, palm trees, and a bar.

16. 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 1,066 total
includes taxes & fees
4 Oct - 5 Oct
American Beech in Greenport - Petite King Room 7
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

17. 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, (33 reviews)
"Home more than exceeded our expectations! There were plenty of different areas for conversation, kitchen was more than well stocked for cooking meals and the place was spotless! View from the back of the house was wonderful, overlooking the golf course and water."
United States
Mark S.
The price is AED 1,208
AED 2,825 total
includes taxes & fees
5 Oct - 6 Oct
Groton Home < 1 Mi to Beach on Long Island Sound!
A wooden pathway leading to a beach with scattered rocks and greenery.

18. 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 900
AED 1,788 total
includes taxes & fees
26 Oct - 27 Oct
Beach Block Hideaway
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

19. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (191 reviews)
"A wonderful stay "
United States
Gina P.
The price is AED 955
AED 1,627 total
includes taxes & fees
19 Oct - 20 Oct
Charming Historic House in Downtown Mystic
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

20. Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Stonington
10.0 out of 10, Exceptional, (73 reviews)
The price is AED 1,322
AED 2,460 total
includes taxes & fees
29 Sep - 30 Sep
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
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

Kenny's Tipperary Inn

Kenny's Tipperary Inn

8/10 Good
"We went on an overnight visit to montauk. It was a bit dated. Sink slow to drain. This could not be corrected as per management. Front desk worker John was very helpful. Otherwise it was perfect for our needs and it was a pet friendly hotel."
Victoria 1-night trip
Posted 3 hours ago
Kenny's Tipperary Inn

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