Southold Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Southold

Fabulous Waterfront Property in the Heart of Wine Country
Sun loungers, beach towels

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (182)
"Beautiful view, clean house, great location "
Fabulous Waterfront Property in the Heart of Wine Country
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is ￥19,697
￥25,756 total
includes taxes & fees
Oct 19 - Oct 20
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is ￥38,881
￥50,918 total
includes taxes & fees
Oct 2 - Oct 3
Cliffside Resort Condominiums
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, (15)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is ￥26,235
￥60,716 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (74)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is ￥8,478
￥25,593 total
includes taxes & fees
Sep 30 - Oct 1
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥29,898
￥50,079 total
includes taxes & fees
Oct 26 - Oct 27
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (190)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is ￥66,598
￥122,374 total
includes taxes & fees
Oct 2 - Oct 3
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Terrace/patio

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is ￥26,759
￥39,256 total
includes taxes & fees
Oct 5 - Oct 6
Shoreline Oasis
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

8.8 out of 10, Excellent, (3)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
The price is ￥26,893
￥35,166 total
includes taxes & fees
Sep 28 - Sep 29
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is ￥8,670
￥25,814 total
includes taxes & fees
Oct 27 - Oct 28
The Mast at Soundview · Beach+Ocean+Sunrise
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, (136)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.2 out of 10, Wonderful, (5)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is ￥7,706
￥24,710 total
includes taxes & fees
Oct 27 - Oct 28
Freeboard at Soundview · Beach+Ocean+Sunrise
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (46)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is ￥53,816
￥104,344 total
includes taxes & fees
Oct 6 - Oct 7
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Outdoor pool, a heated pool

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

10.0 out of 10, Exceptional, (88)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

Stunning Hampton Holiday Family Fantasy for your Team

10.0 out of 10, Exceptional, (73)
"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
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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!"
Rachel 1-night trip
Posted 3 days ago
Ocean Vista Resort

Find out more about Southold

Find out more about Southold

Search for holiday rentals in Southold on Expedia! You can easily find your home rentals, villas, holiday apartments in Southold using one of the methods below:

  • View our selection of featured holiday rentals in Southold
  • Use the map to find apartments and other holiday homes in the Southold neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southold while they last

Look no further and take a look at our great range of rental properties in Southold!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : Visitors like this Southold vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Southold?

With 124 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?

McCabe's Beach and Horton Lane 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.