Holiday Homes in Montauk

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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 €215
includes taxes & fees
9 Apr - 10 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 €545
includes taxes & fees
14 Apr - 15 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 €270
includes taxes & fees
12 Apr - 13 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)
"We loved stayed in your 1776 historical Mystic Seaport cottage. The 6 college roommates enjoyed every minute of our stay and the accommodations were most comfortable. Thanks again. We will hopefully be back!"
United States
Christine
The price is €371
includes taxes & fees
15 Apr - 16 Apr
Charming Historic House in Downtown Mystic

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 €396
includes taxes & fees
9 Apr - 10 Apr
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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 €438
includes taxes & fees
12 Apr - 13 Apr
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

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 €471
includes taxes & fees
5 May - 6 May
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 €654
includes taxes & fees
20 Apr - 21 Apr
Sherman Cottage on the Beach

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 €229
includes taxes & fees
9 Apr - 10 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.
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

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 Blue Anchor House · walk Mystic-Train/Aquarium

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 €1,218
includes taxes & fees
29 Apr - 30 Apr
Walk to Mansion Beach, Large Yard!

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 €664
includes taxes & fees
14 Apr - 15 Apr
Northfork Townhouse walk to all

Newly Renovated Sag Harbor Beach House with Pool

Newly Renovated Sag Harbor Beach House with Pool
Sag Harbor
The price is €576
includes taxes & fees
9 Apr - 10 Apr
Newly Renovated Sag Harbor Beach House with Pool

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, (21 reviews)
"Great house and incredible location. Very attentive hosts. Wonderful place to stay!"
United States
Philip M.
The price is €642
includes taxes & fees
29 Apr - 30 Apr
NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining

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 €528
includes taxes & fees
13 Apr - 14 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.
Charming Mystic Cottage — Walk to Downtown, Spacious & Perfect for Groups!

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 €540
includes taxes & fees
12 Apr - 13 Apr
Harbor View Landing Mystic CT - The Mystic Waterfront House - Third Floor Only

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

Harbor View Landing - The Mystic Waterfront House - Second Floor Only
West Mystic
9.6 out of 10, Exceptional, (8 reviews)
"Awesome time, nice and peaceful "
United States
Dion B.
The price is €546
includes taxes & fees
12 Apr - 13 Apr
Harbor View Landing - The Mystic Waterfront House - Second Floor Only

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 €1,141
includes taxes & fees
11 Apr - 12 Apr
Work and Play Special! Extended Stay Discount
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 Holiday Homes information

Number of reviews
743
Accommodation
117 Holiday Homes
Lowest Price
€215
Highest Price
€1,218

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