A calm lake with a forest in the background during sunset.

Search Vacation Homes in Southold

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Southold vacation homes

Terrace/patio

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)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AED 1,502
AED 2,132 total
includes taxes & fees
29 Jul - 30 Jul
American Beech in Greenport - Petite King Room 7
Beach

Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (7 reviews)
"Everything was so nice and clean. Location was great, walking distance from everything. My children had an amazing time. I would book this again in the summer."
United States
Jessica0610@gmail.com A.
The price is AED 1,818
AED 2,975 total
includes taxes & fees
29 Jul - 30 Jul
Beach Block Hideaway
Sun loungers, beach towels

The SandPiper

The SandPiper
Pipes Cove
9.8 out of 10, Exceptional, (44 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is AED 1,451
AED 2,375 total
includes taxes & fees
16 Aug - 17 Aug
The SandPiper
Sun loungers, beach towels

Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (39 reviews)
"great anf friendly, clean"
United States
Sophia
The price is AED 1,818
AED 2,854 total
includes taxes & fees
12 Aug - 13 Aug
Aqua Vista
Exterior

Beach House

Beach House
East Lyme
9.6 out of 10, Exceptional, (61 reviews)
"Joseph was an excellent, very responsive host. House was very clean and well appointed. We had an excellent time there with our family. "
United States
Enrique
The price is AED 826
AED 1,347 total
includes taxes & fees
3 Aug - 4 Aug
Beach House
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is AED 1,733
AED 3,299 total
includes taxes & fees
30 Jul - 31 Jul
Rogers Lake House (87) · CT College+Beach+USCGA
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 AED 1,572
AED 6,314 total
includes taxes & fees
3 Aug - 4 Aug
BlackBerry Private home with jacuzzi yearlong
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
Black Swan Beachfront Home with Jacuzzi year round
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
"This was the perfect spot for us for a quick weekend stay in Hampton Bays. Close to Ponquoge Beach, restaurants, stores, etc. Great size for our group of four. We didn’t get a chance to use the pool because we didn’t get the good weather, but we will be back. Good value for price. Irina was excellent at communicating. We loved our short stay here. Would highly recommend to my friends."
United States
Eileen O.
The price is AED 1,157
AED 2,371 total
includes taxes & fees
14 Aug - 15 Aug
Hampton Bays Townhouse - Pool, Beach Access
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 reviews)
"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)."
United States
Sarah G.
The price is AED 1,093
AED 2,192 total
includes taxes & fees
26 Aug - 27 Aug
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor dining

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AED 2,725
AED 9,086 total
includes taxes & fees
9 Aug - 10 Aug
Villa Luz Family Home w/ heated pool & jacuzzi
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is AED 1,286
AED 2,373 total
includes taxes & fees
27 Jul - 28 Jul
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"perfect for families"
United States
Okito H.
The price is AED 2,314
AED 4,939 total
includes taxes & fees
27 Jul - 28 Jul
Minutes from the beach, brand new 4 bedroom
Property grounds

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is AED 1,723
AED 2,417 total
includes taxes & fees
29 Jul - 30 Jul
American Beech in Greenport - Deluxe King 6
Coffee/tea maker, fridge, microwave, oven

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 AED 2,020
AED 3,454 total
includes taxes & fees
29 Jul - 30 Jul
Immaculate Waterfront 2 bedroom!
Beach nearby

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is AED 1,837
AED 3,058 total
includes taxes & fees
31 Jul - 1 Aug
adorable ranch in beach community
Beach nearby, sun loungers, beach towels

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is AED 2,281
AED 4,415 total
includes taxes & fees
27 Jul - 28 Jul
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is AED 8,573
AED 12,247 total
includes taxes & fees
16 Aug - 17 Aug
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Interior

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is AED 11,019
AED 16,055 total
includes taxes & fees
27 Jul - 28 Jul
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"The room was clean and beautiful. The grounds and pools were also nice and well kept. The lady at the front desk wasn’t very friendly during check in and also never called like she said she would when the room was ready. I got the room at exactly 4:00 when I returned to the office for the third time. We were also never informed the night we arrived had $1 oysters in the bar which would have been nice to know. In addition, the beach parking pass was helpful but was available first come first serve starting at 8:00 so we had to wake up and go to the desk early to ensure availability. I was also not told that it would cost $5 on my card when checking out. Finally, we were informed coffee was complimentary for guests. After eating in the restaurant we were charged $7 per person for a cup of coffee. When asked about the complimentary coffee for guests we were then told it’s only complimentary to go. If we had known that we would have ordered our very over priced breakfast to go and received the complimentary coffee to enjoy on the table outside our room. Besides the lack of clear communication by the staff, our stay was pleasant and the hotel was comfortable."
Cheryl 2-night trip
Posted less than an hour ago
The Hampton Maid