Holiday Rentals in Montauk

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Our top choices for Montauk holiday rentals

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1266)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is €152
includes taxes & fees
15 Dec - 16 Dec
Montauk Manor

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is €563
includes taxes & fees
15 Dec - 16 Dec
Offshore Residences

Waverly Suite 1 on the Beach

Waverly Suite 1 on the Beach
New Shoreham
9.8 out of 10, Exceptional, (8)
"Cute, convenient, walking distance to downtown and ferry. Host was very responsive. Only downside was size for 3 adults. A bit cramped but would have been perfect for a couple. "
United States
Amy M.
The price is €398
includes taxes & fees
17 Dec - 18 Dec
Waverly Suite 1 on the Beach

Mansion Beach- October to May Available!

Mansion Beach- October to May Available!
New Shoreham
9.4 out of 10, Exceptional, (28)
"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."
United States
Lori W.
The price is €716
includes taxes & fees
15 Dec - 16 Dec
Mansion Beach- October to May Available!

Waverly Suite 2 on the Beach

Waverly Suite 2 on the Beach
New Shoreham
10.0 out of 10, Exceptional, (6)
"Was very clean,reasonable in the price,enjoyed it alot"
United States
Charlotte
The price is €407
includes taxes & fees
15 Dec - 16 Dec
Waverly Suite 2 on the Beach

Waverly Suite 3 on the Beach

Waverly Suite 3 on the Beach
New Shoreham
9.4 out of 10, Exceptional, (6)
"Overall, we had a really excellent stay. The apartment was very clean with a lot of items that looked brand new. The king bed was very comfortable, and we appreciated access to linens, towels, and a washer and dryer. The location was ideal, except for hearing some loud music, from nearby bars, on weekend nights."
United States
Katherine B.
The price is €525
includes taxes & fees
27 Dec - 28 Dec
Waverly Suite 3 on the Beach

Stevedore Landing-#3 · walk downtown Mystic · train · aquarium

Stevedore Landing-#3 · walk downtown Mystic · train · aquarium
Stonington
10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The apartment is in excellent condition."
United States
Marcell
The price is €187
includes taxes & fees
12 Jan - 13 Jan 2026
Stevedore Landing-#3 · walk downtown Mystic · train · aquarium

Super Cute & Cozy Apartment in Downtown Mystic!

Super Cute & Cozy Apartment in Downtown Mystic!
Mystic
9.6 out of 10, Exceptional, (81)
"Cons: Door lock issue, no heat first night. You need new sheets. Grab bar in the shower would be a plus. "
United States
Charlene f.
The price is €176
includes taxes & fees
22 Dec - 23 Dec
Super Cute & Cozy Apartment in Downtown Mystic!

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, (158)
"Nice spot - about as close as you can get to the restaurants and shops downtown, but still quiet. "
United States
Bryan M.
The price is €228
includes taxes & fees
15 Dec - 16 Dec
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,

Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,
The Borough
10.0 out of 10, Exceptional, (71)
"Very quiet neighborhood was a very enjoyable stay would highly recommend "
United States
Jennifer S.
Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
Stonington
10.0 out of 10, Exceptional, (5)
"Great stay with friends! "
United States
Danielle V.
The price is €203
includes taxes & fees
13 Jan - 14 Jan 2026
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

2-bedroom apartment with Ocean Views in Stonington Borough

2-bedroom apartment with Ocean Views in Stonington Borough
2.0 star property
The Borough
The price is €262
includes taxes & fees
15 Dec - 16 Dec
2-bedroom apartment with Ocean Views in Stonington Borough

The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (6)
"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. "
United States
Norma B.
The price is €309
includes taxes & fees
17 Dec - 18 Dec
The Blue Anchor House · walk Mystic-Train/Aquarium

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, (8)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
United States
David C.
The price is €316
includes taxes & fees
6 Jan - 7 Jan 2026
The Mystic Harbor House · walk downtown Mystic · train · aquarium

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
West Mystic
9.8 out of 10, Exceptional, (17)
"We had a wonderful time, great place which was like a small resort. Beautiful views and it was quiet and so peaceful there. We’re looking forward to staying again."
United States
Michael V.
The price is €407
includes taxes & fees
10 Jan - 11 Jan 2026
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Beach Cottage 1 Mile From Weekapaug & Misquamicut

Beach Cottage 1 Mile From Weekapaug & Misquamicut
Westerly
9.0 out of 10, Wonderful, (187)
"Good location, had lots of fun with a group of friends, beautiful neighborhood. Overall just a great stay."
United States
Noah F.
The price is €698
includes taxes & fees
31 Dec - 1 Jan 2026
Beach Cottage 1 Mile From Weekapaug & Misquamicut

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Stonington
10.0 out of 10, Exceptional, (17)
"We were here to meet up with family and thought the apartment was gorgeous! Great stay and would recommend in Mystic."
United States
Lydia D.
The price is €234
includes taxes & fees
15 Dec - 16 Dec
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

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, (9)
"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 €792
includes taxes & fees
31 Dec - 1 Jan 2026
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium

Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium
Stonington
10.0 out of 10, Exceptional, (10)
"Nice location, easy access to downtown Mystic. Nice compliment of amenities. "
United States
Karen B.
The price is €170
includes taxes & fees
11 Jan - 12 Jan 2026
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium

Carrick Landing-#4 · walk Mystic-Train/EV Lvl-2 · aquarium

Carrick Landing-#4 · walk Mystic-Train/EV Lvl-2 · aquarium
Stonington
10.0 out of 10, Exceptional, (2)
"Clean, brand new, very easy. The sleep sofa was even comfortable!"
United States
Maria S.
The price is €253
includes taxes & fees
3 Jan - 4 Jan 2026
Carrick Landing-#4 · walk Mystic-Train/EV Lvl-2 · aquarium
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

Everything you need to know about Montauk holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montauk holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montauk holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montauk holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montauk. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montauk holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montauk holiday rentals we have selected for you start as low as €152 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montauk rentals

At Expedia, we put the best Montauk holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montauk rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montauk holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montauk. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Montauk?

Yes, there are holiday rentals close to the most popular sights in Montauk, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Montauk speak positively about the scenic seaside and top-notch restaurants in this destination. Allow some time to check out the waterfront during your trip.

What are some of the best holiday rentals that Montauk has to offer?

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready: This highly rated holiday home rental in Montauk is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Montauk?

Choose from 339 Expedia holiday rentals in Montauk for a memorable holiday.

What can I see and do in Montauk?

South Edison Beach and Ditch Plains Beach are a couple of scenic spots to enjoy the outdoors, whereas Second House Museum is one of the cultural attractions. Other places in town to visit include Montauk Downs State Park Golf Course and Montauk Downs State Park.

What are holiday rentals like in Montauk?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montauk. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.