Holiday Homes in Southold

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Southold

Our top choices for Southold holiday homes

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
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is NZ$1,009
includes taxes & fees
7 Sept - 8 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (69)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
Stunning Hampton Holiday Family Fantasy for your Team
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Smart TV

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

10.0 out of 10, Exceptional, (6)
"The is great!!! Very convenient location and plenty to do."
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
Terrace/patio

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

10.0 out of 10, Exceptional, (2)
"The aptly named Charming East Hampton Cottage was a beautiful oasis with lush gardens and comfortable accommodations. The host was very gracious and friendly and communicated with us as soon as we booked the home. My only regret was that we couldnt stay longer."
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
Exquisite New Hampton Home in a Perfect Location
Interior

Exquisite New Hampton Home in a Perfect Location

10.0 out of 10, Exceptional, (4)
"Awesome modern home in quiet neighborhood, with beautiful open kitchen and comfortable bedrooms and bathrooms. The outdoor decks and pool were great for lounging and relaxing. The owners were very attentive with communication and the check in process seamless. All around great experience. "
Exquisite New Hampton Home in a Perfect Location
The Cooper-Burke House
Beach nearby, beach towels

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice property, conveniently located, great host!"
The Cooper-Burke House
Another rental season is coming up.
Exterior

Another rental season is coming up.

10.0 out of 10, Exceptional, (19)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Property grounds

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

9.0 out of 10, Wonderful, (2)
"Perfect location."
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Charming beach home, complete with pool & cozy guest house!
Interior

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (31)
"It was very comfortable and cozy, a very great place to spend with your loved ones, very spacious and had everything we needed to enjoy our stay."
Charming beach home, complete with pool & cozy guest house!
Brand New Beach House In Amagansett
Interior

Brand New Beach House In Amagansett

Brand New Beach House In Amagansett
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Walk to town, Bike to beach, Private pool oasis !
Outdoor pool

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
The price is NZ$711
includes taxes & fees
25 Aug - 26 Aug
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is NZ$1,556
includes taxes & fees
26 Aug - 27 Aug
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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 were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is NZ$2,448
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
Aqua Vista
Sun-loungers, beach towels

Aqua Vista

10.0 out of 10, Exceptional, (18)
"This was our second stay at Aqua Vista. We love the property. The house is recently renovated and everything is brand new. It is nicely decorated and very comfortable. It is located close to the beach and center of the town with all of the restaurants. The property manager is a great host. We enjoyed our visit to the fullest."
Aqua Vista
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

Hotel Indigo East End by IHG

Hotel Indigo East End by IHG

10/10 Excellent
"Everything was great"
Louis 3-night trip
Posted 14 hours ago
Hotel Indigo East End by IHG