Holiday Homes in Montauk

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Featured Holiday Homes in Montauk and around

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Fridge, microwave, oven, stovetop

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 €317
includes taxes & fees
3 Nov - 4 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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 €265
includes taxes & fees
13 Oct - 14 Oct
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

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 €349
includes taxes & fees
15 Oct - 16 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Property grounds

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 €269
includes taxes & fees
9 Oct - 10 Oct
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Sun-loungers, beach towels

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 €581
includes taxes & fees
29 Oct - 30 Oct
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
The Blue Anchor House · walk Mystic-Train/Aquarium
Terrace/patio

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 €334
includes taxes & fees
4 Nov - 5 Nov
The Blue Anchor House · walk Mystic-Train/Aquarium
Charming Historic House in Downtown Mystic
Smart TV, video games, books, stereo

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 €351
includes taxes & fees
9 Oct - 10 Oct
Charming Historic House in Downtown Mystic
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is €267
includes taxes & fees
9 Oct - 10 Oct
American Beech in Greenport - Petite King Room 7
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Dining

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 €429
includes taxes & fees
5 Nov - 6 Nov
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Terrace/patio

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

10.0 out of 10, Exceptional, (91)
"Great location responsive hosts fully stocked cozy accommodations "
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Mansion Beach- October to May Available!
On the beach, sun-loungers

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 €760
includes taxes & fees
20 Oct - 21 Oct
Mansion Beach- October to May Available!
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Smart TV, fireplace

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 €635
includes taxes & fees
23 Oct - 24 Oct
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Beach Cottage 1 Mile From Weekapaug & Misquamicut
Beach

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 €480
includes taxes & fees
23 Oct - 24 Oct
Beach Cottage 1 Mile From Weekapaug & Misquamicut
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Exterior

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

10.0 out of 10, Exceptional, (51)
"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 €558
includes taxes & fees
9 Oct - 10 Oct
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
Exterior

Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY

10.0 out of 10, Exceptional, (5)
"Wonderful place for family fun!"
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
Luxe Historic Bungalow in Heart of Downtown Mystic
Fridge, microwave, oven, stovetop

Luxe Historic Bungalow in Heart of Downtown Mystic

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay. The house is in a perfect location to town. The house is beautiful and so comfortable. Owners are very easy to communicate with. They were lovely and accommodating. We very much enjoyed our stay and hope to be back."
Luxe Historic Bungalow in Heart of Downtown Mystic
Sherman Cottage on the Beach
TV, offices

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 €739
includes taxes & fees
22 Oct - 23 Oct
Sherman Cottage on the Beach
Downtown Mystic Waterfront Oasis
Outdoor dining

Downtown Mystic Waterfront Oasis

2.0 star property
10.0 out of 10, Exceptional, (15)
"Great stay within minutes from downtown Mystic. Definitely coming back!"
Downtown Mystic Waterfront Oasis
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (44)
"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 €3,080
includes taxes & fees
20 Oct - 21 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Charming Northfork Townhouse- walk to all
Fridge, microwave, oven, stovetop

Charming Northfork Townhouse- walk to all

10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
The price is €616
includes taxes & fees
9 Oct - 10 Oct
Charming Northfork Townhouse- walk to all
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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Wonderful views and spacious studio. Very clean and well maintained. "
Kevin 2-night trip
Posted 5 days ago
Beachcomber Resort at Montauk

Find out more about Montauk

Find out more about Montauk

Montauk Holiday Homes information

Number of reviews
826
Accommodation
125 Holiday Homes
Lowest Price
€265
Highest Price
€3,080

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