A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

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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 Southampton holiday homes

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

1. 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 £718
includes taxes & fees
21 Oct - 22 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A modern living room with a sofa, armchairs, a coffee table, and a TV.

2. 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.
The price is £1,070
includes taxes & fees
27 Sept - 28 Sept
Minutes from the beach, brand new 3 bedroom
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

3. 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 £1,090
includes taxes & fees
1 Oct - 2 Oct
Minutes from the beach, brand new 4 bedroom
A wooden gate partially covered by lush green ivy.

4. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is £2,763
includes taxes & fees
7 Oct - 8 Oct
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

5. 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 £1,997
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated Pristine Southampton Colonial
A wooden house with a front porch, white railings, and a double door.

6. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is £2,175
includes taxes & fees
6 Oct - 7 Oct
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern building with large windows overlooking a beach.

7. 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 £917
includes taxes & fees
29 Sept - 30 Sept
Beachfront Jacuzzi All Year - Black Swan Home
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)
The price is £1,263
includes taxes & fees
29 Sept - 30 Sept
Jacuzzi year-round - Villa Luz Private Home
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

9. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (3 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

10. 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 £466
includes taxes & fees
17 Oct - 18 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A dining area with a round table, six chairs, and a chandelier.

11. 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 £990
includes taxes & fees
27 Sept - 28 Sept
Year round Jacuzzi - Blackberry Home
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (46 reviews)
The price is £242
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

13. 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 £732
includes taxes & fees
29 Sept - 30 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

14. 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 £798
includes taxes & fees
26 Sept - 27 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A beach with people relaxing, a pier extending into the water, and a clear sky.

15. 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 £325
includes taxes & fees
4 Oct - 5 Oct
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A rectangular swimming pool with a pebble border and a fire feature in the center.

16. 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 £697
includes taxes & fees
8 Oct - 9 Oct
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

17. 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 £702
includes taxes & fees
29 Sept - 30 Sept
Immaculate Waterfront 2 bedroom!
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 £235
includes taxes & fees
7 Oct - 8 Oct
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

19. 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 £370
includes taxes & fees
15 Oct - 16 Oct
Beach Block Hideaway
A coastal hotel with multiple buildings, a swimming pool, and a beach view.

20. 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 £487
includes taxes & fees
27 Sept - 28 Sept
Unit 1311: Cottage | Garden View | Deuce
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 Southampton Hotel Reviews

Hamlet Inn

Hamlet Inn

10/10 Excellent
"The hotel location is ideal. About a 2 mile radius from the town center, shopping, attractions and beaches. The room is very comfortable where all necessary amenity items are available. We had a nice closet in the room, a refrigerator and microwave. It would have been nice to have a couple of drawers if we had stayed more than 2 nights. The shower was particularly nice! Coffe, tea, soft drinks along with a wide variety of snacks, cakes and candy bars are available the entire day."
Niel 2-night trip
Posted 3 days ago
Hamlet Inn

Find out more about Southampton

Southampton Holiday Homes information

Number of reviews
275
Accommodation
194 Holiday Homes
Lowest Price
£235
Highest Price
£2,763