Holiday Homes in Montauk

Start date: Check-in selected.
To Date
End date: Check-out

    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
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Featured Holiday Homes in Montauk

Children’s area
New Construction full of amenities
New Construction full of amenities
2.0 star property
The price is AU$1,201
includes taxes & fees
18 Oct - 19 Oct
New Construction full of amenities
TV, offices
Sherman Cottage on the Beach
Sherman Cottage on the Beach
10.0 out of 10, Exceptional, (4)
"Quaint, clean cottage, perfectly situated among shops, restaurants, beach, and ferry - all accessible on foot. "
The price is AU$1,305
includes taxes & fees
19 Oct - 20 Oct
Sherman Cottage on the Beach
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (9)
"Open concept home beautiful with private yard space. It was perfect for our stay"
The price is AU$560
includes taxes & fees
3 Nov - 4 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Terrace/patio
The Blue Anchor House · walk Mystic-Train/Aquarium
The Blue Anchor House · walk Mystic-Train/Aquarium
10.0 out of 10, Exceptional, (5)
"This was an adorable house with great access to downtown Mystic. The house is well updated and very clean. We would stay here again for sure. It was a very comfortable experience. "
The price is AU$558
includes taxes & fees
20 Oct - 21 Oct
The Blue Anchor House · walk Mystic-Train/Aquarium
Fridge, microwave, oven, stovetop
Cozy quiet gem, private & fenced in backyard
Cozy quiet gem, private & fenced in backyard
9.4 out of 10, Exceptional, (3)
"good times"
The price is AU$1,407
includes taxes & fees
20 Oct - 21 Oct
Cozy quiet gem, private & fenced in backyard
Property grounds
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
9.8 out of 10, Exceptional, (155)
"Very cute stay in a historic house. Great location for downtown and great to have a parking spot. LOVED the porch. Location is louder as the walls are thin. Would stay here again!"
The price is AU$508
includes taxes & fees
17 Nov - 18 Nov
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Dining
The Mystic Harbor House · walk downtown Mystic · train · aquarium
The Mystic Harbor House · walk downtown Mystic · train · aquarium
10.0 out of 10, Exceptional, (5)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
The price is AU$648
includes taxes & fees
10 Nov - 11 Nov
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Outdoor pool, a heated pool
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is AU$9,021
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Outdoor pool, a heated pool
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is AU$615
includes taxes & fees
26 Oct - 27 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Terrace/patio
American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"Great job "
The price is AU$473
includes taxes & fees
19 Oct - 20 Oct
American Beech in Greenport - Petite King Room 7
Smart TV, video games, books, stereo
Charming Historic House in Downtown Mystic
Charming Historic House in Downtown Mystic
10.0 out of 10, Exceptional, (156)
"Such a unique home in the lovely town! Much to see and do. We need a longer stay. Thank you. "
The price is AU$626
includes taxes & fees
28 Oct - 29 Oct
Charming Historic House in Downtown Mystic
Exterior
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.
10.0 out of 10, Exceptional, (52)
"One of the best VRBO rentals we have had. Host was communicative. House was prepared, clean, comfortable, and centrally located, just steps from the Seaport and 5 minutes from town. Would recommend highly."
The price is AU$985
includes taxes & fees
19 Oct - 20 Oct
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Sun-loungers, beach towels
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
10.0 out of 10, Exceptional, (125)
"Excellent stay! Where else could you accommodate 8 people with 4 king size beds and all the kitchen and housekeeping supplies you need. Well thought out and very comfortable outside and interior areas to relax in.Just a great experience"
The price is AU$968
includes taxes & fees
19 Oct - 20 Oct
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Outdoor pool, a heated pool
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
10.0 out of 10, Exceptional, (45)
"Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. "
The price is AU$5,311
includes taxes & fees
28 Oct - 29 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Smart TV, fireplace
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
9.8 out of 10, Exceptional, (7)
"Overall a great stay. The kids didn't want to leave and neither did we."
The price is AU$1,084
includes taxes & fees
23 Oct - 24 Oct
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.
Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is AU$9,980
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach
Beach Cottage 1 Mile From Weekapaug & Misquamicut
Beach Cottage 1 Mile From Weekapaug & Misquamicut
9.0 out of 10, Wonderful, (184)
"Good location, had lots of fun with a group of friends, beautiful neighborhood. Overall just a great stay."
The price is AU$823
includes taxes & fees
23 Oct - 24 Oct
Beach Cottage 1 Mile From Weekapaug & Misquamicut
TV, stereo
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only
10.0 out of 10, Exceptional, (11)
"Great home and location, and Mystic is a gem"
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only
On the beach, sun-loungers
Mansion Beach- October to May Available!
Mansion Beach- October to May Available!
9.2 out of 10, Wonderful, (26)
"This was a great place for an extended family. The space and yard were nice, with great proximity to the beach and Andy's Way."
The price is AU$1,342
includes taxes & fees
26 Oct - 27 Oct
Mansion Beach- October to May Available!
Dining
8- Heart of Mystic, lovely home with water views
8- Heart of Mystic, lovely home with water views
9.4 out of 10, Exceptional, (16)
"We had a wonderful weekend, house is roomy and comfortable!"
The price is AU$1,449
includes taxes & fees
16 Nov - 17 Nov
8- Heart of Mystic, lovely home with water views
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

Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"Great Option."
Robert 1-night trip
Posted 1 day ago
Aqualina Inn Montauk

Find out more about Montauk

Montauk Holiday Homes information

Number of reviews
735
Accommodation
120 Holiday Homes
Lowest Price
AU$473
Highest Price
AU$9,980

Explore a world of travel with Expedia