A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Vacation Rentals in Town of Southampton

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Our top choices for Town of Southampton vacation rentals

A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

1. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is ￥70,817
￥154,085 total
includes taxes & fees
Oct 4 - Oct 5
Elegant 5-Bedroom Hamptons Home with Private Pool
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

2. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is ￥42,490
￥90,439 total
includes taxes & fees
Oct 1 - Oct 2
Immaculate Waterfront 2 bedroom!
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

3. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is ￥188,844
￥246,500 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Hamptons Escape 3BR Minutes From Beach!
A covered patio with a table and chairs, large windows, and a view of greenery.

4. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is ￥55,080
￥92,416 total
includes taxes & fees
Oct 4 - Oct 5
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A modern building with large windows overlooking a beach.

5. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is ￥26,281
￥194,284 total
includes taxes & fees
Oct 12 - Oct 13
Beachfront Jacuzzi All Year - Black Swan Home
Roger’s Beach

6. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
The price is ￥55,080
￥102,667 total
includes taxes & fees
Oct 1 - Oct 2
Prime location, walk to all, cozy cottage WHB
A modern living room with a sofa, armchairs, a coffee table, and a TV.

7. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
Minutes from the beach, brand new 3 bedroom
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

8. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥17,625
￥264,155 total
includes taxes & fees
Oct 4 - Oct 5
Jacuzzi year-round - Villa Luz Private Home
A small cabin with a porch, surrounded by trees and a fenced area.

9. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥46,424
￥96,549 total
includes taxes & fees
Oct 4 - Oct 5
Lovely studio with AC in charming Sag Harbor
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

10. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is ￥138,171
￥260,781 total
includes taxes & fees
Oct 28 - Oct 29
Amazing Southampton Home with Private Heated Pool
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 ￥52,326
￥102,217 total
includes taxes & fees
Oct 13 - Oct 14
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A modern living room with a grey sofa, round coffee table, and a white fireplace.

12. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is ￥263,752
￥435,643 total
includes taxes & fees
Oct 1 - Oct 2
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

13. 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.
The price is ￥89,229
￥175,303 total
includes taxes & fees
Oct 1 - Oct 2
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

14. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is ￥240,776
￥350,062 total
includes taxes & fees
Oct 1 - Oct 2
Lovely & Spacious Sag Harbor escape with heated pool
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

15. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is ￥70,817
￥174,582 total
includes taxes & fees
Oct 1 - Oct 2
Minutes from the beach, brand new 4 bedroom
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

16. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is ￥317,116
￥471,260 total
includes taxes & fees
Oct 4 - Oct 5
Newly Renovated Pristine Southampton Colonial
A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

17. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is ￥13,534
￥73,160 total
includes taxes & fees
Oct 2 - Oct 3
Steps to the beach | Seabreeze Cottage #3
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

18. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ￥70,817
￥150,311 total
includes taxes & fees
Oct 21 - Oct 22
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

19. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

20. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is ￥22,661
￥50,165 total
includes taxes & fees
Oct 6 - Oct 7
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
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 Town of Southampton Hotel Reviews

Southampton Inn

Southampton Inn

8/10 Good
"The check-in date of 4PM in the afternoon was a turn off given you are paying foe the full day. Bit of a money grab. Further the gentleman at the front desk who checked us in when we got there was arrogant. Otherwise a nice stay."
Catherine 4-night trip
Posted 6 hours ago
Southampton Inn

Find out more about Town of Southampton

Vacation Apartments in Town of Southampton

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