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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 NZ$1,744
includes taxes & fees
19 Oct - 20 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 NZ$1,126
includes taxes & fees
27 Sept - 28 Sept
Unit 1311: Cottage | Garden View | Deuce
A dining area with a round table, six chairs, and a chandelier.

3. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry 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 NZ$2,223
includes taxes & fees
27 Sept - 28 Sept
Year round Jacuzzi - Blackberry Home
A rectangular swimming pool with a pebble border and a fire feature in the center.

4. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
The price is NZ$1,623
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
A two-story house with a porch and a wooden picnic table in the front yard.

5. 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, (189 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is NZ$494
includes taxes & fees
27 Sept - 28 Sept
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

6. 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 NZ$1,833
includes taxes & fees
21 Oct - 22 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.

7. 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 NZ$1,768
includes taxes & fees
26 Oct - 27 Oct
Unit 511: Cottage | Ocean View | Nautilus
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

8. 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 NZ$620
includes taxes & fees
26 Oct - 27 Oct
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is NZ$553
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

10. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (46 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$553
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.

11. 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 NZ$881
includes taxes & fees
20 Oct - 21 Oct
The Blue Anchor House · walk Mystic-Train/Aquarium
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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$748
includes taxes & fees
28 Sept - 29 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

13. 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 NZ$1,094
includes taxes & fees
11 Oct - 12 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A two-story house with a front porch, a black door, and a mailbox.

14. 3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (33 reviews)
"We will be back! great, responsive owners, phenomenal property and location! Go get breakfast at The Eatery down the road, it’s amazing!!"
United States
Travis C.
The price is NZ$1,216
includes taxes & fees
29 Sept - 30 Sept
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

15. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton Home < 1 Mi to Beach on Long Island Sound!
Groton
10.0 out of 10, Exceptional, (33 reviews)
"Home more than exceeded our expectations! There were plenty of different areas for conversation, kitchen was more than well stocked for cooking meals and the place was spotless! View from the back of the house was wonderful, overlooking the golf course and water."
United States
Mark S.
The price is NZ$1,401
includes taxes & fees
5 Oct - 6 Oct
Groton Home < 1 Mi to Beach on Long Island Sound!
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, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$847
includes taxes & fees
4 Oct - 5 Oct
Beach Block Hideaway
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

17. Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Stonington
10.0 out of 10, Exceptional, (72 reviews)
"Loved our stay, beautifully decorated inside and out. Conveniently located and so much within walking distance."
United States
Deborah J
The price is NZ$1,197
includes taxes & fees
27 Sept - 28 Sept
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
An outdoor dining area with hanging lights, palm trees, and a bar.

18. 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 NZ$529
includes taxes & fees
5 Oct - 6 Oct
American Beech in Greenport - Petite King Room 7
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

19. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (191 reviews)
"A wonderful stay "
United States
Gina P.
The price is NZ$816
includes taxes & fees
19 Oct - 20 Oct
Charming Historic House in Downtown Mystic
A covered patio with a wooden table and white chairs, large windows, and a view of a deck and trees.

20. 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 NZ$1,229
includes taxes & fees
8 Oct - 9 Oct
The Mystic Harbor House · walk downtown Mystic · train · 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

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"it was a lovely stay at the Ocean surf resort. We went in September and the weather was spectacular. We really enjoyed watching the sea life from the deck. We saw so many whales, dolphins and seals too. It was quiet enough to get a night's sleep and the mattress was pretty good too. My only issue was the kitchenette- which was there but not usable. There is no counter space at all. I really think that the rooms need to be reconfigured. There was a nice working little fridge. We never used the stove top (I think that it should be taken out) or just mount the microwave. But all in all, we would stay here again."
Donovan 3-night trip
Posted 2 days ago
Ocean Surf Resort

Find out more about Montauk

Montauk Holiday Homes information

Number of reviews
879
Accommodation
76 Holiday Homes
Lowest Price
NZ$494
Highest Price
NZ$2,223

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