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Top Holiday Rentals in Montauk

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

9.8 out of 10, Exceptional, (156)
"Great location. Very nice property. Made the weekend stay a success "
The price is £197
includes taxes & fees
21 Jul - 22 Jul
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

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

The price is £296
includes taxes & fees
21 Jul - 22 Jul
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

10.0 out of 10, Exceptional, (7)
"Open concept home beautiful with private yard space. It was perfect for our stay"
The price is £381
includes taxes & fees
23 Jul - 24 Jul
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (8)
"Great place! Great communication with property owner!"
The price is £487
includes taxes & fees
27 Jul - 28 Jul
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Harper House Downtown Mystic Romantic Weekend Getaway

9.8 out of 10, Exceptional, (32)
"We thoroughly enjoyed our stay here. "
The price is £400
includes taxes & fees
10 Aug - 11 Aug
Harper House Downtown Mystic Romantic Weekend Getaway

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

10.0 out of 10, Exceptional, (119)
"Beautiful, everything that you need, spotless, great family accommodations..."
The price is £538
includes taxes & fees
23 Jul - 24 Jul
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Charming 1-bedroom private suite in exclusive neighborhood house in Amagansett

8.0 out of 10, Very good, (1)
The price is £642
includes taxes & fees
21 Jul - 22 Jul
Charming 1-bedroom private suite in exclusive neighborhood house in Amagansett

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
The price is £303
includes taxes & fees
22 Jul - 23 Jul
American Beech in Greenport - Petite King Room 7

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 £404
includes taxes & fees
21 Jul - 22 Jul
The Mystic Harbor House · walk downtown Mystic · train · aquarium

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 "
The price is £693
includes taxes & fees
28 Jul - 29 Jul
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY

10.0 out of 10, Exceptional, (5)
"Wonderful place for family fun!"
The price is £393
includes taxes & fees
31 Jul - 1 Aug
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

8.0 out of 10, Very good, (1)
"Overall a great stay. The kids didn't want to leave and neither did we."
The price is £688
includes taxes & fees
27 Jul - 28 Jul
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

9.8 out of 10, Exceptional, (149)
"Super time. Property is confidently located which made it easy to walk everywhere."
The price is £346
includes taxes & fees
3 Aug - 4 Aug
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Luxe Historic Bungalow in Heart of Downtown Mystic

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay. The house is in a perfect location to town. The house is beautiful and so comfortable. Owners are very easy to communicate with. They were lovely and accommodating. We very much enjoyed our stay and hope to be back."
The price is £847
includes taxes & fees
23 Jul - 24 Jul
Luxe Historic Bungalow in Heart of Downtown Mystic

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

10.0 out of 10, Exceptional, (64)
"Great spot and beautiful home!"
The price is £682
includes taxes & fees
27 Jul - 28 Jul
Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,

The Blue Anchor House · walk Mystic-Train/Aquarium

10.0 out of 10, Exceptional, (3)
"This was an adorable house with great access to downtown Mystic. The house is well updated and very clean. We would stay here again for sure. It was a very comfortable experience. "
The price is £462
includes taxes & fees
27 Jul - 28 Jul
The Blue Anchor House · walk Mystic-Train/Aquarium

Stylish Coastal Home with Private Beach Access & Outdoor Shower – Pet Friendly!

10.0 out of 10, Exceptional, (1)
"The house and location were great. It is under 5 minute walk to the beach. It is a great beach for little kids. The house has a well stocked kitchen and beach stuff. Marie was very responsive and checked on us regularly to see if we needed anything. The neighborhood was quiet we went for walks every night. We highly recommend."
The price is £862
includes taxes & fees
15 Aug - 16 Aug
Stylish Coastal Home with Private Beach Access & Outdoor Shower – Pet Friendly!

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 £554
includes taxes & fees
27 Jul - 28 Jul
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

Bay Access Cottage + Pilates Gym

2.0 star property
The price is £397
includes taxes & fees
31 Jul - 1 Aug
Bay Access Cottage + Pilates Gym

Mystic Coastal Gem: 3BR Ideal for Families!

10.0 out of 10, Exceptional, (33)
"It was a wonderful stay! Perfect location, amenities and fun!"
The price is £488
includes taxes & fees
28 Jul - 29 Jul
Mystic Coastal Gem: 3BR Ideal for Families!
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

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. Our travellers also rate Relaxing Lake Montauk Retreat as a favourite home for rent in Montauk.

How many holiday rentals are there in Montauk?

Choose from 432 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 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.