A lighthouse on a rocky outcrop with a grassy area and buildings nearby.

Holiday Homes in Montauk

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Montauk holiday homes

A sandy beach path with wooden fencing leading to the ocean.

1. Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower

Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
Culloden Shores
8.6 out of 10, Excellent, (4 reviews)
"Definitely more space than expected, and super close to everything in Montauk. Planning on coming back next year!"
United States
Nick M.
The price is €841
includes taxes & fees
7 Oct - 8 Oct
Montauk Beach Retreat — 3BR, Steps to Beach, BBQ, Patio & Outdoor Shower
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

2. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is €550
includes taxes & fees
12 Oct - 13 Oct
Unit 1311: Cottage | Garden View | Deuce
A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is €1,139
includes taxes & fees
7 Oct - 8 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

4. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is €951
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH
A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

5. Unit 511: Cottage | Ocean View | Nautilus

Unit 511: Cottage | Ocean View | Nautilus
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
The price is €693
includes taxes & fees
12 Oct - 13 Oct
Unit 511: Cottage | Ocean View | Nautilus
A two-story house with a porch and a wooden picnic table in the front yard.

6. 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, (191 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is €234
includes taxes & fees
2 Nov - 3 Nov
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A living room with a fireplace, a grey armchair, and a large window.

7. 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, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €483
includes taxes & fees
5 Nov - 6 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

8. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is €224
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

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

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic River Historic District
9.8 out of 10, Exceptional, (178 reviews)
"Great location "
United States
Brian S.
The price is €279
includes taxes & fees
4 Nov - 5 Nov
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
An outdoor dining area with hanging lights, palm trees, and a bar.

10. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is €279
includes taxes & fees
7 Oct - 8 Oct
American Beech in Greenport - Petite King Room 7
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

11. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is €569
includes taxes & fees
13 Oct - 14 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A beach with people relaxing, a pier extending into the water, and a clear sky.

12. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is €333
includes taxes & fees
3 Nov - 4 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

13. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is €286
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

14. The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (10 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 price is €412
includes taxes & fees
3 Nov - 4 Nov
The Blue Anchor House · walk Mystic-Train/Aquarium
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

15. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (193 reviews)
"A wonderful stay "
United States
Gina P.
The price is €387
includes taxes & fees
19 Oct - 20 Oct
Charming Historic House in Downtown Mystic
A wooden pathway leading to a beach with scattered rocks and greenery.

16. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is €390
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway
A modern living room with a fireplace, a large window with a view of a beach, and a 'Welcome to the Farm' sign.

17. Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT

Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Groton
10.0 out of 10, Exceptional, (142 reviews)
"Loved the woods next to it. The stained glass were very cool"
United States
Kate R.
The price is €713
includes taxes & fees
18 Oct - 19 Oct
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

18. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A covered patio with a wooden table and white chairs, large windows, and a view of a deck and trees.

19. The Mystic Harbor House · walk downtown Mystic · train · aquarium

The Mystic Harbor House · walk downtown Mystic · train · aquarium
Stonington
9.8 out of 10, Exceptional, (11 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 €487
includes taxes & fees
3 Nov - 4 Nov
The Mystic Harbor House · walk downtown Mystic · train · aquarium
A small kitchen with a view of the water, a bar area with stools, and a sign that reads "the BLUFFS".

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

Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
West Mystic
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place for family fun!"
United States
nancy m.
The price is €398
includes taxes & fees
8 Oct - 9 Oct
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Great"
Dillon 1-night trip
Posted 1 hour ago
Offshore Montauk

Find out more about Montauk

Montauk Holiday Homes information

Number of reviews
887
Accommodation
73 Holiday Homes
Lowest Price
€224
Highest Price
€1,139

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