Holiday Homes in Montauk

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Montauk and around

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Fridge, microwave, oven, stovetop

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

9.8 out of 10, Exceptional, (162)
"Very nice!"
The price is €227
includes taxes & fees
7 Sept - 8 Sept
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
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 €330
includes taxes & fees
9 Sept - 10 Sept
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
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 €405
includes taxes & fees
26 Aug - 27 Aug
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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, (119)
"Short family get together since we couldn’t do it for Christmas! Lots of fun and laughs food and drink. Great house in a great location! Close to everything and all the amenities!"
The price is €584
includes taxes & fees
3 Sept - 4 Sept
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
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, (152)
"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 €323
includes taxes & fees
23 Sept - 24 Sept
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
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, (13)
"Great place! Great communication with property owner!"
The price is €516
includes taxes & fees
7 Sept - 8 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Mystic Coastal Gem: 3BR Ideal for Families!
Outdoor dining

Mystic Coastal Gem: 3BR Ideal for Families!

10.0 out of 10, Exceptional, (35)
"It was a wonderful stay! Perfect location, amenities and fun!"
The price is €515
includes taxes & fees
26 Aug - 27 Aug
Mystic Coastal Gem: 3BR Ideal for Families!
The Blue Anchor House · walk Mystic-Train/Aquarium
Terrace/patio

The Blue Anchor House · walk Mystic-Train/Aquarium

10.0 out of 10, Exceptional, (4)
"Check-in was easy. We were delighted when we entered to find an immaculate home, beautifully furnished, with everything clean & easy to find. Very easy access to local attractions. "
The price is €446
includes taxes & fees
31 Aug - 1 Sept
The Blue Anchor House · walk 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, (90)
"We loved the house with it's history everywhere you looked. We also were impressed with all the cooking tools available "
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
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
Beach Cottage 1 Mile From Weekapaug & Misquamicut
Beach

Beach Cottage 1 Mile From Weekapaug & Misquamicut

9.0 out of 10, Wonderful, (180)
"Cute house in a great location by the beach!"
The price is €540
includes taxes & fees
7 Sept - 8 Sept
Beach Cottage 1 Mile From Weekapaug & Misquamicut
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 €313
includes taxes & fees
1 Sept - 2 Sept
American Beech in Greenport - Petite King Room 7
Downtown Mystic Waterfront Oasis
Outdoor dining

Downtown Mystic Waterfront Oasis

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay within minutes from downtown Mystic. Definitely coming back!"
The price is €623
includes taxes & fees
26 Aug - 27 Aug
Downtown Mystic Waterfront Oasis
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Exterior

Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

10.0 out of 10, Exceptional, (49)
"Amazing home away from home. Very clean and walkable. It was a perfect girls trip weekend "
The price is €667
includes taxes & fees
26 Aug - 27 Aug
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Cozy quiet gem, private & fenced in backyard
Fridge, microwave, oven, stovetop

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
Cozy quiet gem, private & fenced in backyard
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, (4)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
The price is €575
includes taxes & fees
24 Sept - 25 Sept
The Mystic Harbor House · walk downtown Mystic · train · aquarium
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, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"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 €1,256
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Terrace/patio

Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Outdoor pool, a heated pool

Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons

10.0 out of 10, Exceptional, (57)
"We had a very nice stay at Stan's house. We spent the majority of our time relaxing in the beautiful backyard. The pool is amazing!"
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montauk Hotel Reviews

Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Staff was extremely helpful. We arrived late. We had requested a first floor room as I am handicapped. We were told only 2nd floor rooms. The woman at the front desk went somewhere, came back and found a first floor room for us.. The room was nice, kind of small, but we managed. It was super clean and neat. The housekeepers kept it that way for entire stay. We needed and extra pillow and tissues. We called the front desk. They came by in just minutes. Lovely experience!"
Lyne Taylor 7-night trip
Posted 1 day ago
Ocean Resort Inn