Montauk Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Montauk holiday rentals

Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,325 reviews)
"Great property "
United States
brian
The price is HK$1,053
HK$1,356 total
includes taxes & fees
22 Apr - 23 Apr
Montauk Manor
Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is HK$1,066
HK$1,303 total
includes taxes & fees
23 Apr - 24 Apr
Montauk Oceanside Suites
Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is HK$1,313
HK$1,926 total
includes taxes & fees
11 May - 12 May
The Surf Club
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is HK$1,220
HK$1,649 total
includes taxes & fees
17 May - 18 May
Driftwood Resort
Living area

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is HK$4,296
HK$5,802 total
includes taxes & fees
29 Apr - 30 Apr
Offshore Residences
Smart TV, books

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, (174 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$1,976 total
includes taxes & fees
19 Apr - 20 Apr
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Flat-screen TV

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,457
HK$1,664 total
includes taxes & fees
21 Apr - 22 Apr
North Fork Cottages & RV Resort
Fridge, microwave, oven, stovetop

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Stonington
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Kerri P.
The price is HK$1,189
HK$2,549 total
includes taxes & fees
24 Apr - 25 Apr
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Fridge, microwave, oven, stovetop

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, (22 reviews)
"Beautiful, quiet, close to town!! Really enjoyed our stay. "
United States
Maureen F.
The price is HK$1,253
HK$2,412 total
includes taxes & fees
20 Apr - 21 Apr
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Interior

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 reviews)
"Great stay with friends! "
United States
Danielle V.
The price is HK$999
HK$2,182 total
includes taxes & fees
20 Apr - 21 Apr
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
Terrace/patio

Waverly Suite 1 on the Beach

Waverly Suite 1 on the Beach
New Shoreham
9.8 out of 10, Exceptional, (8 reviews)
"Cottage was adorable and just as advertised. Great location and steps to Baby Beach. The views were lovely. Host was super responsive and even accommodated us when the ferries were canceled due to TV r hurricane. A great little gem downtown! "
United States
Lee Ann F.
The price is HK$1,120
HK$3,348 total
includes taxes & fees
30 Apr - 1 May
Waverly Suite 1 on the Beach
Property grounds

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)
"Great stay no problems. Awesome location, good communication. Would stay again!"
United States
Sherry B.
The price is HK$1,146
HK$2,460 total
includes taxes & fees
21 Apr - 22 Apr
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Exterior detail

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, (18 reviews)
"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 HK$1,559
HK$1,988 total
includes taxes & fees
21 Apr - 22 Apr
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
Exterior detail

Unbeatable Downtown Mystic Location

Unbeatable Downtown Mystic Location
Groton
10.0 out of 10, Exceptional, (12 reviews)
"This is hands down one of the nicest places we have stayed. Very updated, all the kitchen amenities we needed and communication was great. We will definitely be retiring! "
United States
Anonymous traveller
The price is HK$1,163
HK$2,382 total
includes taxes & fees
22 Apr - 23 Apr
Unbeatable Downtown Mystic Location
Exterior

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$1,827
HK$5,313 total
includes taxes & fees
20 Apr - 21 Apr
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is HK$1,128
HK$1,629 total
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums
Exterior

Riverbed, Romantic Waterfront Suite, walk to town<br><br>

Riverbed, Romantic Waterfront Suite, walk to town<br><br>
Stonington
9.8 out of 10, Exceptional, (45 reviews)
"The property was very nice, well appointed, Just what we were looking for."
United States
Karen B.
The price is HK$1,551
HK$2,870 total
includes taxes & fees
29 Apr - 30 Apr
Riverbed, Romantic Waterfront Suite, walk to town<br><br>
Interior

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 &amp; Jessica V.
The price is HK$2,269
HK$3,948 total
includes taxes & fees
5 May - 6 May
Charming Historic House in Downtown Mystic
Exterior

3 BR Retreat 1 Mile from Westerly’s Beaches! 1 King, 4 Queen Beds& Pull Out Sofa

3 BR Retreat 1 Mile from Westerly’s Beaches! 1 King, 4 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (17 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$1,527
HK$4,250 total
includes taxes & fees
14 May - 15 May
3 BR Retreat 1 Mile from Westerly’s Beaches! 1 King, 4 Queen Beds& Pull Out Sofa
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is HK$1,160
HK$1,538 total
includes taxes & fees
30 Apr - 1 May
Windward Shores Ocean Resort
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

Montauk Manor

Montauk Manor

10/10 Excellent
"We stayed in a 1 bedroom deluxe loft. Only downfall is how much and how loud the noise travels throughout the unit. Next stay will definitely be a 2 bedroom."
Karen 2-night trip
Posted 16 hours ago
Montauk Manor

Find out more about Montauk

Search for holiday rentals in Montauk on Expedia! You can easily find your home rentals, villas, holiday apartments in Montauk using one of the methods below:

  • View our selection of featured holiday rentals in Montauk
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  • Enter your travel dates to view the best deals on holiday rentals in Montauk while they last

Look no further and take a look at our great range of rental properties in Montauk!

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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Montauk?

Choose from 334 Expedia holiday rentals in Montauk for a memorable holiday.

What can I see and do in Montauk?

South Edison Beach and Kirk Park 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 Shadmoor State Park 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.