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

Search Vacation Homes in Montauk

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house and great location! "
United States
John C.
The price is ￥72,481
￥168,798 total
includes taxes & fees
Sep 30 - Oct 1
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
A dining area with a round table, six chairs, and a chandelier.

2. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 ￥68,390
￥273,239 total
includes taxes & fees
Sep 8 - Sep 9
BlackBerry Private home with jacuzzi yearlong
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

3. 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, (1 review)
"Great clean beautiful property."
United States
ANGELA S.
The price is ￥86,287
￥187,490 total
includes taxes & fees
Sep 27 - Sep 28
Spacious house in East Hampton with heated pool + WFH
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

4. East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (2 reviews)
"We have just returned from an amazing summer experience in East Hampton! From the minute I secured the booking to checkout, everything was perfectly smooth! The house was so wonderful, every design detail and amenity…. It was truly like the best of all possible creature comforts…. Fully stocked kitchen, incredible fire pit for late evening s’mores, extraordinary huge pool, patio with outdoor speakers, and enough indoor space meticulously designed and decorated that proved our dream vacation...
United States
GINA W.
The price is ￥96,030
￥216,407 total
includes taxes & fees
Sep 16 - Sep 17
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
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, (186 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is ￥19,974
￥46,459 total
includes taxes & fees
Sep 23 - Sep 24
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.

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.
The price is ￥29,860
￥76,666 total
includes taxes & fees
Sep 9 - Sep 10
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

7. 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 ￥45,540
￥93,290 total
includes taxes & fees
Sep 20 - Sep 21
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A wooden pathway leading to a beach with scattered rocks and greenery.

8. 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 ￥31,159
￥66,636 total
includes taxes & fees
Sep 7 - Sep 8
Beach Block Hideaway
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, (175 reviews)
"Great location "
United States
Brian S.
The price is ￥32,250
￥62,057 total
includes taxes & fees
Sep 30 - Oct 1
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

10. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is ￥28,043
￥55,407 total
includes taxes & fees
Sep 10 - Sep 11
The SandPiper
A beach with waves gently lapping onto the shore under a clear sky.

11. Beach Cottage 1 Mile From Weekapaug & Misquamicut

Beach Cottage 1 Mile From Weekapaug & Misquamicut
Westerly
8.8 out of 10, Excellent, (196 reviews)
"This place met all our needs. "
United States
Andrea G.
The price is ￥28,762
￥68,674 total
includes taxes & fees
Sep 15 - Sep 16
Beach Cottage 1 Mile From Weekapaug & Misquamicut
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, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥31,159
￥61,342 total
includes taxes & fees
Sep 8 - Sep 9
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 ￥31,095
￥74,246 total
includes taxes & fees
Sep 8 - Sep 9
The Blue Anchor House · walk Mystic-Train/Aquarium
A beach with people relaxing, a pier extending into the water, and a clear sky.

14. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥28,043
￥67,820 total
includes taxes & fees
Sep 8 - Sep 9
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
An outdoor dining area with hanging lights, palm trees, and a bar.

15. 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 ￥47,777
￥69,739 total
includes taxes & fees
Sep 8 - Sep 9
American Beech in Greenport - Petite King Room 7
A covered patio with a wooden table and white chairs, large windows, and a view of a deck and trees.

16. 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)
"Location Location Location!"
United States
Liz T.
The price is ￥50,660
￥99,374 total
includes taxes & fees
Sep 9 - Sep 10
The Mystic Harbor House · walk downtown Mystic · train · aquarium
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

17. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is ￥117,925
￥213,778 total
includes taxes & fees
Sep 15 - Sep 16
Work and Play Special! Extended Stay Discount
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

18. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (186 reviews)
"A wonderful stay "
United States
Gina P.
The price is ￥47,937
￥82,452 total
includes taxes & fees
Sep 23 - Sep 24
Charming Historic House in Downtown Mystic
A small kitchen with a view of the water, a bar area with stools, and a sign that reads "the BLUFFS".

19. 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 ￥95,714
￥123,813 total
includes taxes & fees
Sep 15 - Sep 16
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
A wooden porch with wicker furniture and a small table, overlooking a green lawn and a house in the background.

20. Perfect Group Escape · Coastal Mystic Ranch

Perfect Group Escape · Coastal Mystic Ranch
Mystic
10.0 out of 10, Exceptional, (39 reviews)
"It was a wonderful stay! Perfect location, amenities and fun!"
United States
Julie S.
The price is ￥63,117
￥101,986 total
includes taxes & fees
Sep 7 - Sep 8
Perfect Group Escape · Coastal Mystic Ranch
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montauk Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great beachfront property! Spa is amazing!"
Daniel 1-night trip
Posted 5 hours ago
Gurney's Montauk Resort & Seawater Spa

Find out more about Montauk

Montauk Vacation Homes information

Number of reviews
1,035
Accommodation
73 Vacation Homes
Lowest Price
￥46,459
Highest Price
￥273,239