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Vacation Homes in Montauk

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

10.0 out of 10, Exceptional, (1)
"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...
The price is ¥25,758
¥52,142 total
includes taxes & fees
Oct 28 - Oct 29
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

9.8 out of 10, Exceptional, (153)
"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 ¥21,534
¥46,085 total
includes taxes & fees
Oct 5 - Oct 6
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is ¥24,375
¥57,781 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

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 ¥16,694
¥52,940 total
includes taxes & fees
Oct 7 - Oct 8
The Blue Anchor House · walk Mystic-Train/Aquarium

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 ¥13,848
¥53,064 total
includes taxes & fees
Nov 3 - Nov 4
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

10.0 out of 10, Exceptional, (124)
"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 ¥46,210
¥97,740 total
includes taxes & fees
Oct 5 - Oct 6
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Mystic Magical Sunsets awaits your arrival

10.0 out of 10, Exceptional, (12)
"Great location. Property is very nice. "
The price is ¥44,724
¥78,810 total
includes taxes & fees
Oct 5 - Oct 6
Mystic Magical Sunsets awaits your arrival

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (155)
"Such a unique home in the lovely town! Much to see and do. We need a longer stay. Thank you. "
The price is ¥30,733
¥58,746 total
includes taxes & fees
Oct 5 - Oct 6
Charming Historic House in Downtown Mystic

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is ¥29,291
¥45,070 total
includes taxes & fees
Oct 7 - Oct 8
American Beech in Greenport - Petite King Room 7

The Mystic Harbor House · walk downtown Mystic · train · aquarium

10.0 out of 10, Exceptional, (5)
"Loved the area. Loved the house. Very clean "
The price is ¥33,955
¥75,212 total
includes taxes & fees
Oct 14 - Oct 15
The Mystic Harbor House · walk downtown Mystic · train · aquarium

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

9.8 out of 10, Exceptional, (7)
The price is ¥51,517
¥106,189 total
includes taxes & fees
Oct 23 - Oct 24
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

10.0 out of 10, Exceptional, (90)
"Great location responsive hosts fully stocked cozy accommodations "
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

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 ¥51,517
¥127,173 total
includes taxes & fees
Oct 13 - Oct 14
Mansion Beach- October to May Available!

Beach Cottage 1 Mile From Weekapaug & Misquamicut

9.0 out of 10, Wonderful, (183)
"Good location, had lots of fun with a group of friends, beautiful neighborhood. Overall just a great stay."
The price is ¥44,157
¥80,754 total
includes taxes & fees
Oct 23 - Oct 24
Beach Cottage 1 Mile From Weekapaug & Misquamicut

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

10.0 out of 10, Exceptional, (50)
"The house is adorable and so nicely appointed. It was a perfect location for a quick walk to downtown or to the Museum. Chris is a fabulous host and so accommodating. We would definitely stay again!"
The price is ¥45,040
¥93,414 total
includes taxes & fees
Oct 6 - Oct 7
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

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"
The price is ¥73,448
¥94,916 total
includes taxes & fees
Oct 16 - Oct 17
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is ¥105,977
¥195,913 total
includes taxes & fees
Oct 5 - Oct 6
Work and Play Special! Extended Stay Discount

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (43)
"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 ¥290,906
¥509,270 total
includes taxes & fees
Oct 27 - Oct 28
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

Block Island The Way It Used To Be!!! Steps From Everything!!!

10.0 out of 10, Exceptional, (36)
"This charming cottage was the ideal home base for our family’s unforgettable week on Block Island! Steps from shops, restaurants, and pristine beaches, the location couldn’t be better. The cottage was spotlessly clean, cozy, and well-equipped, making our stay a breeze. The owner was incredibly responsive, ensuring everything was perfect. Highly recommend this gem for your island getaway!"
The price is ¥80,856
¥154,167 total
includes taxes & fees
Oct 12 - Oct 13
Block Island The Way It Used To Be!!! Steps From Everything!!!

Downtown Mystic Waterfront Oasis

2.0 star property
10.0 out of 10, Exceptional, (14)
"Great stay within minutes from downtown Mystic. Definitely coming back!"
Downtown Mystic Waterfront Oasis
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

Find out more about Montauk

Find out more about Montauk

Montauk Vacation Homes information

Number of reviews
8,339
Accommodation
125 Vacation Homes
Lowest Price
¥19,490
Highest Price
¥58,685