Montgomery Cottages - Vacation Rentals in Hamptons

Seabreeze #4 - Charming Cottage Footsteps to the Beach From US $816
         

Hampton Bays Retreat: Walk to Squires Beach! From US $540
         

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8.0 (2 Reviews)
Cottage
  • Air Conditioner
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Hither Hills 2BR Montauk Cottage - walk to beach! From US $113
         

9.8 (9 Reviews)
Cottage
  • Air Conditioner
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  • TV
Fairy Tale Guest Cottage in Magic Garden by Pool From US $411
         

10.0 (76 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Hamptons Waterfront- Great Location! From US $658
         

10.0 (40 Reviews)
Cottage
  • Air Conditioner
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  • TV
Cute East Hampton Cottage w/Patio - Walk to Beach From US $431
         

Luxury Places to Stay in Hamptons

Over 5349+ Luxury Places to Stay in or Near Hamptons
Villa Tide From US $18,853
         

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New
Villa
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  • Pool

Top-Rated Vacation Rentals with a Pool in Hamptons

Over 3446+ Top-Rated Vacation Rentals with a Pool in or Near Hamptons

Pet-Friendly Vacation Rentals in Hamptons

Over 2174+ Pet-Friendly Vacation Rentals in or Near Hamptons
Villa Red Hut From US $2,616
         

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New
Villa
  • Air Conditioner
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  • Pet Friendly
Canoe Place Waterfront Residences From US $2,053
         

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10.0 (1 Review)
Condo
  • Parking
  • Pet Friendly
  • Pool
See More Pet-Friendly Vacation Rentals in Hamptons on PetFriendly.io

Large Vacation Homes & Villas in Hamptons

Over 1844+ Large Vacation Homes & Villas in or Near Hamptons
Villa Florencia - Luxuriant 11 Bedroom Villa From US $4,668
         

Summer getaway From US $868
         

9.2 (12 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
Fantastic Family & Friends Getaway Montauk House - Any Season! From US $2,767
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Hamptons

Over 133+ Wheelchair Accessible Vacation Homes in or Near Hamptons
Montauk Mansion INDOOR + OUTDOOR POOLS From US $302
         

9.6 (103 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
East Hampton Art House Bed & Breakfast From US $499
         

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9.6 (65 Reviews)
Bed & Breakfast
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  • Pool
New and Ready for Summer 2026! 5-Stars From US $926
         

10.0 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
MONTAUK MANOR-DELUXE STUDIO APARTMENT From US $221
         

9.8 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Hamptons Varoom and Airbnb Places to Stay Under $200

Over 76+ Hamptons Varoom and Airbnb Places to Stay Under $200
Town walking distance-Bridgehampton Cottage From US $162
         

9.4 (10 Reviews)
Cottage
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  • Pet Friendly
Royal Atlantic Beach Resort From US $109
         

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7.5 (992 Reviews)
Resort
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Carole's Place B & B From US $171
         

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9.8 (61 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Beachwood Cove by RoveTravel | 3BR w/Heated Pool From US $196
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly Listed The Sunlit Cozy Cottage by the Sea on Lake Montauk From US $195
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
OceanView Studio 3 Twin Pond From US $163
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1-bedroom with WiFi and AC in brilliant Montauk From US $139
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Hamptons

Over 1881+ Instantly Bookable Vacation Homes in or Near Hamptons
Cozy sun drenched beach cottage private beach, walk to town, hot tub From US $490
         

Sag Harbor Village Gem From US $743
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Amazing Location 2-bedroom Townhouse - Sleeps 8 From US $1,535
         

10.0 (27 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

About Hamptons Vacation Rentals

With more than 209 Hamptons vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Hamptons.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Hamptons, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Hamptons. Places to stay near Hamptons are 484.14 ft² on average, with prices averaging $791 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Hamptons with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Hamptons

Type Count
Cottages 201
Vacation Homes 7
Hotels with Suites 1

Use these Quick Filters to Find a Vacation Rental in Hamptons

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Hamptons.

Weather in Hamptons

View the weather forecast for Hamptons before booking your Hamptons Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F