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Our top choices for Montauk vacation 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, (176 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 ¥14,916
¥39,292 total
includes taxes & fees
May 4 - May 5
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 ¥30,805
¥98,156 total
includes taxes & fees
May 4 - May 5
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

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 ¥28,329
¥74,017 total
includes taxes & fees
May 6 - May 7
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (7 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 ¥27,317
¥68,775 total
includes taxes & fees
May 4 - May 5
The Blue Anchor House · walk Mystic-Train/Aquarium

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, (168 reviews)
"Great stay no problems. Awesome location, good communication. Would stay again!"
United States
Sherry B.
The price is ¥16,408
¥40,357 total
includes taxes & fees
May 4 - May 5
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, (173 reviews)
"Super cute house! Perfect for a stay to view the area! "
United States
Rocky & Jessica V.
The price is ¥31,088
¥60,402 total
includes taxes & fees
May 4 - May 5
Charming Historic House in Downtown Mystic

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 ¥34,621
¥85,348 total
includes taxes & fees
May 5 - May 6
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

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 ¥39,724
¥121,178 total
includes taxes & fees
May 4 - May 5
Sherman Cottage on the Beach

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 ¥54,954
¥71,048 total
includes taxes & fees
May 4 - May 5
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (19 reviews)
"Awesome stay host we’re phenomenal beautiful clean house "
United States
Adrian V.
The price is ¥62,804
¥129,769 total
includes taxes & fees
May 14 - May 15
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

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)
"Location Location Location!"
United States
Liz T.
The price is ¥31,364
¥73,882 total
includes taxes & fees
May 4 - May 5
The Mystic Harbor House · walk downtown Mystic · train · aquarium

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 ¥31,245
¥48,076 total
includes taxes & fees
May 4 - May 5
American Beech in Greenport - Petite King Room 7

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 ¥54,404
¥107,899 total
includes taxes & fees
May 4 - May 5
Renovated Townhouse walk to all

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 ¥52,991
¥106,106 total
includes taxes & fees
May 4 - May 5
Northfork 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 ¥52,079
¥118,062 total
includes taxes & fees
May 4 - May 5
NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining

In Town Hideaway for a Block Island Getaway!!!

In Town Hideaway for a Block Island Getaway!!!
New Shoreham
9.6 out of 10, Exceptional, (38 reviews)
"We had a great stay!"
United States
Jack B.
The price is ¥109,907
¥204,408 total
includes taxes & fees
Jun 1 - Jun 2
In Town Hideaway for a Block Island Getaway!!!

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 ¥67,200
¥222,001 total
includes taxes & fees
May 10 - May 11
BlackBerry Private home with jacuzzi yearlong

Downtown Mystic Waterfront Oasis

Downtown Mystic Waterfront Oasis
Groton
10.0 out of 10, Exceptional, (17 reviews)
"Great stay within minutes from downtown Mystic. Definitely coming back!"
United States
Jessica D.
The price is ¥86,356
¥131,967 total
includes taxes & fees
May 21 - May 22
Downtown Mystic Waterfront Oasis

Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only

Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only
West Mystic
10.0 out of 10, Exceptional, (11 reviews)
"Just a great experience overall "
United States
Clifford D.
The price is ¥78,348
¥101,248 total
includes taxes & fees
May 4 - May 5
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only

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 ¥95,384
¥167,637 total
includes taxes & fees
May 4 - May 5
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
870
Accommodation
93 Vacation Homes
Lowest Price
¥39,292
Highest Price
¥222,001