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

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 ￥65,638
￥159,721 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥17,776
￥207,901 total
includes taxes & fees
Sep 28 - Sep 29
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 ￥50,968
￥101,523 total
includes taxes & fees
Sep 27 - Sep 28
Unit 1311: Cottage | Garden View | Deuce
A two-story house with a porch and a wooden picnic table in the front yard.

4. 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, (188 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is ￥19,664
￥45,581 total
includes taxes & fees
Sep 28 - Sep 29
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

5. 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 ￥93,285
￥160,200 total
includes taxes & fees
Oct 4 - Oct 5
Unit 511: Cottage | Ocean View | Nautilus
A living room with a fireplace, a grey armchair, and a large window.

6. 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.
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

7. 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 ￥70,790
￥168,407 total
includes taxes & fees
Oct 19 - Oct 20
Spacious house in East Hampton with heated pool + WFH
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

8. 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 ￥35,395
￥66,188 total
includes taxes & fees
Oct 13 - Oct 14
Charming Historic House in Downtown Mystic
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. 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 ￥22,830
￥50,370 total
includes taxes & fees
Oct 18 - Oct 19
The SandPiper
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

10. 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 ￥27,514
￥53,484 total
includes taxes & fees
Oct 7 - Oct 8
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

11. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,810
￥48,527 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

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 Blue Anchor House · walk Mystic-Train/Aquarium
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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥27,608
￥66,950 total
includes taxes & fees
Sep 28 - Sep 29
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

14. 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 ￥36,056
￥54,326 total
includes taxes & fees
Sep 30 - Oct 1
American Beech in Greenport - Petite King Room 7
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 ￥47,235
￥109,670 total
includes taxes & fees
Sep 29 - Sep 30
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

16. 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 ￥51,801
￥126,779 total
includes taxes & fees
Oct 5 - Oct 6
Groton Home < 1 Mi to Beach on Long Island Sound!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

17. 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 ￥52,306
￥102,178 total
includes taxes & fees
Oct 4 - Oct 5
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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, (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 ￥38,541
￥76,026 total
includes taxes & fees
Oct 4 - Oct 5
Beach Block Hideaway
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

19. 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, (71 reviews)
"Loved our stay, beautifully decorated inside and out. Conveniently located and so much within walking distance."
United States
Deborah J
The price is ￥56,632
￥110,078 total
includes taxes & fees
Sep 24 - Sep 25
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

20. 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 ￥89,274
￥175,391 total
includes taxes & fees
Sep 24 - Sep 25
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I really love this hotel! The rooms are beautiful, the service is excellent, and I’ve had a great experience every time I’ve stayed there. I’ve been a few times already and will definitely be coming back next year!"
Veronika 2-night trip
Posted 3 hours ago
Montauk Yacht Club

Find out more about Montauk

Montauk Vacation Homes information

Number of reviews
879
Accommodation
73 Vacation Homes
Lowest Price
￥45,581
Highest Price
￥207,901