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Our top choices for Montauk holiday homes

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, (173 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is HK$744
HK$1,975 total
includes taxes & fees
21 Apr - 22 Apr
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

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

Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Mystic
10.0 out of 10, Exceptional, (92 reviews)
"House was well appointed and very clean and comfortable. Really appreciated the extras...coffee supplies and toiletries."
United States
Stephanie P.
The price is HK$1,536
HK$4,896 total
includes taxes & fees
15 Apr - 16 Apr
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

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

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic
9.8 out of 10, Exceptional, (166 reviews)
"Very welcoming, clean, lots of personality"
United States
Christine B.
The price is HK$965
HK$2,228 total
includes taxes & fees
15 Apr - 16 Apr
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (172 reviews)
"Super cute house! Perfect for a stay to view the area! "
United States
Rocky & Jessica V.
The price is HK$1,832
HK$3,384 total
includes taxes & fees
15 Apr - 16 Apr
Charming Historic House in Downtown Mystic

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
West Mystic
10.0 out of 10, Exceptional, (3 reviews)
"We had a lovely experience in West Mystick at the Harbor House. The rental was lovely, clean, and contained enough of the necessary amenities. The view of the harbor was lovely. There were renters below us that had small children and at times that was very noisy. You could hear them running back and forth most of the evening. If they were playing music you could hear that as well. It was very cold during our time in Mystic so the heat was necessary. The baseboard heat was sufficient to keep...
United States
Suzanne S.
The price is HK$2,741
HK$3,543 total
includes taxes & fees
15 Apr - 16 Apr
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

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, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is HK$1,776
HK$4,139 total
includes taxes & fees
12 May - 13 May
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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

Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Groton
10.0 out of 10, Exceptional, (131 reviews)
"The house was very clean. We thoroughly enjoyed our stay. The host was very communicative and provided everything we needed. Thank you!"
United States
Karolina Z.
The price is HK$1,825
HK$4,386 total
includes taxes & fees
5 May - 6 May
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (6 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 HK$1,514
HK$3,619 total
includes taxes & fees
15 Apr - 16 Apr
The Blue Anchor House · walk Mystic-Train/Aquarium

Sherman Cottage on the Beach

Sherman Cottage on the Beach
New Shoreham
10.0 out of 10, Exceptional, (4 reviews)
"Quaint, clean cottage, perfectly situated among shops, restaurants, beach, and ferry - all accessible on foot. "
United States
Kathleen P.
The price is HK$1,981
HK$6,044 total
includes taxes & fees
26 Apr - 27 Apr
Sherman Cottage on the Beach

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"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"
United States
Beth R.
The price is HK$2,079
HK$4,558 total
includes taxes & fees
15 Apr - 16 Apr
Northfork Townhouse walk to all

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,323
HK$2,085 total
includes taxes & fees
15 Apr - 16 Apr
American Beech in Greenport - Petite King Room 7

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!
Westerly
9.8 out of 10, Exceptional, (16 reviews)
"Property was amazing...plenty of room for the whole family and close to the beaches and aquarium! We will be staying again! "
United States
Erin f.
The price is HK$3,524
HK$6,990 total
includes taxes & fees
17 Apr - 18 Apr
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is HK$2,396
HK$4,974 total
includes taxes & fees
15 Apr - 16 Apr
Renovated Townhouse walk to all

NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining

NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining
Mystic
10.0 out of 10, Exceptional, (22 reviews)
"Great house and incredible location. Very attentive hosts. Wonderful place to stay!"
United States
Philip M.
The price is HK$2,439
HK$5,463 total
includes taxes & fees
15 Apr - 16 Apr
NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining

Walk to Mansion Beach, Large Yard!

Walk to Mansion Beach, Large Yard!
New Shoreham
9.4 out of 10, Exceptional, (28 reviews)
"This place is great. Great location. Clean."
United States
Jason A.
The price is HK$5,716
HK$11,015 total
includes taxes & fees
29 Apr - 30 Apr
Walk to Mansion Beach, Large Yard!

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 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 HK$1,034
HK$5,797 total
includes taxes & fees
19 Apr - 20 Apr
BlackBerry Private home with jacuzzi yearlong

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

The Mystic Harbor House · walk downtown Mystic · train · aquarium
Stonington
9.6 out of 10, Exceptional, (9 reviews)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
United States
David C.
The price is HK$1,796
HK$3,990 total
includes taxes & fees
20 Apr - 21 Apr
The Mystic Harbor House · walk downtown Mystic · train · aquarium

Charming Mystic Cottage — Walk to Downtown, Spacious & Perfect for Groups!

Charming Mystic Cottage — Walk to Downtown, Spacious & Perfect for Groups!
Groton
10.0 out of 10, Exceptional, (3 reviews)
"The Ashby Cottage was a wonderful winter getaway for our family. It was literally walking distance to downtown Mystic and easily accessible. The house was clean and beautifully decorated. The bedrooms were spacious and super comfortable. The fact they offered Disney was a bonus for the kiddos! I would definitely recommend for any family or large group!"
United States
Nancy M.
The price is HK$2,349
HK$5,059 total
includes taxes & fees
30 Apr - 1 May
Charming Mystic Cottage — Walk to Downtown, Spacious & Perfect for Groups!

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is HK$5,638
HK$10,423 total
includes taxes & fees
15 Apr - 16 Apr
Work and Play Special! Extended Stay Discount

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is HK$4,405
HK$7,896 total
includes taxes & fees
15 Apr - 16 Apr
Beachfront Greenport Villa
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

Montauk Vacation Homes information

Number of reviews
750
Accommodation
89 Vacation Homes
Lowest Price
HK$1,975
Highest Price
HK$11,015

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