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

Southold Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Southold vacation rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
"Great stay & great staff!"
United States
James
The price is AED 899
AED 1,027 total
includes taxes & fees
28 Jun - 29 Jun
North Fork Resort
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 569
AED 1,013 total
includes taxes & fees
1 Jul - 2 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AED 807
AED 1,756 total
includes taxes & fees
28 Jun - 29 Jun
Adorable Cottage, 5 min walk to water & town
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, (8 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 559
AED 1,788 total
includes taxes & fees
28 Jun - 29 Jun
Rogers Lake House (87) · CT College+Beach+USCGA
Living area

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The price is AED 1,267
AED 2,634 total
includes taxes & fees
22 Jul - 23 Jul
The Beach Nest-Lux Cottage Steps to the Beach
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AED 596
AED 1,125 total
includes taxes & fees
29 Jun - 30 Jun
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV, offices

Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is AED 316
AED 1,691 total
includes taxes & fees
28 Jun - 29 Jun
Seabreeze #3 Cozy Cottage steps to the beach
1 bedroom, bed sheets

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is AED 789
AED 1,187 total
includes taxes & fees
15 Jul - 16 Jul
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is AED 789
AED 1,196 total
includes taxes & fees
5 Jul - 6 Jul
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
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.
The price is AED 801
AED 4,887 total
includes taxes & fees
30 Jun - 1 Jul
Black Swan Beachfront Home with Jacuzzi year round
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 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 415
AED 3,733 total
includes taxes & fees
28 Jun - 29 Jun
BlackBerry Private home with jacuzzi yearlong
Smart TV, books

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Old Lyme
The price is AED 413
AED 775 total
includes taxes & fees
29 Jun - 30 Jun
Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Beach nearby, sun loungers, beach towels

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
The price is AED 1,319
AED 2,414 total
includes taxes & fees
8 Jul - 9 Jul
Beach Cottage, private beach and pass
Beach nearby

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
The price is AED 658
AED 1,206 total
includes taxes & fees
29 Jun - 30 Jun
Keel at Soundview · Beach+OceanView+Sunrise
Fridge, microwave, oven, stovetop

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 1,157
AED 1,842 total
includes taxes & fees
1 Jul - 2 Jul
The gardners Cottage 1 mile from long Island Sound - pet friendly
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, (25 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 411
AED 6,165 total
includes taxes & fees
30 Jun - 1 Jul
Villa Luz Family Home w/ heated pool & jacuzzi
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 757
AED 1,759 total
includes taxes & fees
29 Jun - 30 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (262 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is AED 1,167
AED 1,493 total
includes taxes & fees
23 Jul - 24 Jul
Cliffside Resort Condominiums
1 bedroom, bed sheets

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is AED 710
AED 1,135 total
includes taxes & fees
28 Jun - 29 Jun
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Dining

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is AED 1,516
AED 2,671 total
includes taxes & fees
24 Jul - 25 Jul
Adorable Cottage with Cottage porch, walk to water & town
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

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Our stay at the Hampton maid was absolute perfection from start to finish. The representative at the front desk, went above and beyond to make us feel welcome, ensuring a seamless check-in and offering incredible personalized recommendations for the area. When we opened the door to our room, we could not believe the features that were offered to us for our stay. Refrigerator was filled with cold beverages for purchase also snacks, and other amenities located on the table near the window. The bathroom products they offered were top notch with incredible fragrances. The linens were crisp and clean, and the comforter was amazing. The pool was clean and inviting while the lounge chairs were comfortable, and they also offered pool towels that were extremely large and thirsty. Our first night we dined in the hotel restaurant and took advantage of the happy hour menu, which was extensive and reasonably priced . The presentation of each item that we ordered was flavorful and delicious. The bartender had extensive knowledge of the wine list and suggestions were also offered by the head chef. Upon the completion of our dinner we return to our room and sat outside on our deck. It felt like we were sitting in a mountain like setting as we enjoyed the serenity of the surroundings. We could not have picked a better spot and amore enjoyable two night retreat. This place is worth every penny"
James Vincent Donohue 2-night trip
Posted 5 hours ago
The Hampton Maid

Frequently asked questions

Can I find a vacation rental in Southold?

Yes, we offer vacation rentals in Southold close to Custer Institute and Observatory, or you can select a secluded option if you're looking for extra privacy while you relax. Southold is known for its wineries and beaches. Make sure you have time to check out the gardens and football games during your trip.

What are some of the best vacation home rentals that Southold has to offer?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: You might want to consider this vacation rental near Southold, which is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Southold?

With 117 Expedia vacation rentals, you're sure to find just the right place for your Southold stay.

What’s there to see and do in Southold?

Horton Lane Beach and McCabe's Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and Croteaux Vineyards are other places worth a visit.

What’s a vacation rental in Southold like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Southold. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.