Holiday Homes in Southold

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Southold and around

Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is €1,022
includes taxes & fees
25 Aug - 26 Aug
Beautifully farmhouse
Cozy quiet gem, private & fenced in backyard
Fridge, microwave, oven, stovetop

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is €1,371
includes taxes & fees
18 Aug - 19 Aug
Cozy quiet gem, private & fenced in backyard
Bay Access Cottage + Pilates Gym
Beach nearby, sun-loungers, beach towels

Bay Access Cottage + Pilates Gym

2.0 star property
The price is €618
includes taxes & fees
9 Sept - 10 Sept
Bay Access Cottage + Pilates Gym
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Private kitchen

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

10.0 out of 10, Exceptional, (1)
"We were escaping NYC for the weekend and exploring real estate in the area. This house was absolutely beautiful and way bigger than we needed. Unfortunately it was rainy out and we really didn’t get to spend too much time in the house since we were driving around it looks like it has a beautiful property with a pool etc. so hopefully we can come back in the summer."
The price is €992
includes taxes & fees
16 Sept - 17 Sept
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is €458
includes taxes & fees
18 Aug - 19 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
The price is €3,899
includes taxes & fees
16 Sept - 17 Sept
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is €6,743
includes taxes & fees
10 Sept - 11 Sept
Sag Harbor Water View w Dock 1.5ml from town
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is €5,638
includes taxes & fees
22 Aug - 23 Aug
Spacious 5-bedroom house with water views and 2 houses from the bay.
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!"
The price is €430
includes taxes & fees
15 Sept - 16 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Outdoor pool, a heated pool

Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons

10.0 out of 10, Exceptional, (57)
"We had a very nice stay at Stan's house. We spent the majority of our time relaxing in the beautiful backyard. The pool is amazing!"
The price is €1,843
includes taxes & fees
25 Aug - 26 Aug
Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons
Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is €14,296
includes taxes & fees
22 Aug - 23 Aug
Stunning Southampton Village Modern Home
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is €1,258
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Terrace/patio

Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is €5,143
includes taxes & fees
3 Sept - 4 Sept
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Pool

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

9.2 out of 10, Wonderful, (9)
"Great location and comfortable home. Easy check in and check out."
The price is €1,246
includes taxes & fees
14 Sept - 15 Sept
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Poolside, Daily Breakfast, Hampstons Style Double
Property grounds

Poolside, Daily Breakfast, Hampstons Style Double

The price is €1,356
includes taxes & fees
9 Sept - 10 Sept
Poolside, Daily Breakfast, Hampstons Style Double
Luxurious 1BR Poolside, Daily Breakfast, Patio
Property grounds

Luxurious 1BR Poolside, Daily Breakfast, Patio

The price is €2,310
includes taxes & fees
18 Aug - 19 Aug
Luxurious 1BR Poolside, Daily Breakfast, Patio
1BR Poolside, Daily Breakfast, Serene Double Suite
Property grounds

1BR Poolside, Daily Breakfast, Serene Double Suite

The price is €2,650
includes taxes & fees
18 Aug - 19 Aug
1BR Poolside, Daily Breakfast, Serene Double Suite
California King Poolside, Daily Breakfast, Minibar
Property grounds

California King Poolside, Daily Breakfast, Minibar

The price is €1,147
includes taxes & fees
3 Sept - 4 Sept
California King Poolside, Daily Breakfast, Minibar
Huge Island Getaway Pool Hot Tub Walk To Beach
Beach nearby

Huge Island Getaway Pool Hot Tub Walk To Beach

10.0 out of 10, Exceptional, (7)
"Property great. Beautiful home with great amenities"
The price is €2,409
includes taxes & fees
31 Aug - 1 Sept
Huge Island Getaway Pool Hot Tub Walk To Beach
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Exterior detail

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

9.8 out of 10, Exceptional, (19)
"House was perfectly appointed in Southampton! Close to all the spots--Southampton town, Bridgehampton shopping and quaint Sag Harbor"
The price is €2,723
includes taxes & fees
24 Aug - 25 Aug
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
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 Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Lovely hotel. Family rooms were very spacious and perfect for the 4 of us. Pool area really clean and lots of sunbeds. Breakfast was great and good choice. We had an issue with a very noisy neighbour, which was dealt with and we were moved rooms the next day, as well as security helping in the night. Riverhead is a nice area, can recommend Cuccino pizza."
Richard 3-night trip
Posted 23 hours ago
Hyatt Place Long Island East End