---
title: "Southold Vacation Rentals from $194: Search Short-Term Rentals | Expedia.com"
description: "Find the best deals on Southold vacation rentals with Expedia.com. We offer a huge selection of top vacation homes for rental in New York. Book your next vacation with us!"
canonical: "https://www.expedia.com/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-13T09:15:02Z
---

Plan your trip

- [Southold Travel Guide](https://www.expedia.com/Southold.dx183719)
- [Hotels in Southold](https://www.expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)
- [Flights to Southold](https://www.expedia.com/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)
- [Things to do in Southold](https://www.expedia.com/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)
- [Car Rentals in Southold](https://www.expedia.com/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)
- [Southold Vacation Packages](https://www.expedia.com/Southold.d183719.Destination-Travel-Guides)

# Southold Vacation Rentals
![A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.](https://images.trvl-media.com/place/183719/b634a311-72c8-4775-8993-a7fef52c97ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

[Check prices for these dates, December 13 – 14, 2026](https://www.expedia.com/Hotel-Search?regionId=183719&startDate=2026-12-13&endDate=2026-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&sort=VACATION%5FRENTAL)

[View in a map](https://www.expedia.com/Hotel-Search?regionId=183719&stayLength=1&daysInFuture=30&pwaOverlay=map)

## Our top choices for Southold vacation rentals

### [1\. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.](https://www.expedia.com/Southold-Hotels-Perfect-For-A-Relaxing-Getaway-Surrounded-By-Nature-Two-Bedroom.h120181056.Hotel-Information)

![A serene lakeside setting with a gazebo and a bird feeder.](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/w3845h1809x0y27-8459e752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Southold
- Guest rating: 9.6/10 (Exceptional, 10 reviews)
- Price: $414 nightly, $473 total, Nov 23 - Nov 24, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay., by Kelly V.

### [2\. Cliffside Resort Condominiums](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9/10 (Wonderful, 299 reviews)
- Price: $301 nightly, $344 total, Nov 29 - Nov 30, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Great condo. Very nice location and grounds., by William

### [3\. North Fork Resort](https://www.expedia.com/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

![A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9.6/10 (Exceptional, 73 reviews)
- Price: $302 nightly, $345 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Everything was perfect 💞, by Altynai

### [4\. Harbor Heights](https://www.expedia.com/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information)

![A beach with people relaxing on chairs and sunbathing.](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pipes Cove
- Guest rating: 10/10 (Exceptional, 29 reviews)
- Price: $194 nightly, $221 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Perfect spot to stay on the North Fork!, by Steven R.

### [5\. The SandPiper](https://www.expedia.com/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information)

![A beach with people sunbathing, a pier extending into the water, and a clear blue sky.](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/a339ae20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pipes Cove
- Guest rating: 9.6/10 (Exceptional, 58 reviews)
- Price: $203 nightly, $232 total, Nov 30 - Dec 1, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :), by Manuela C.

### [6\. Aqua Vista](https://www.expedia.com/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information)

![A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pipes Cove
- Guest rating: 10/10 (Exceptional, 54 reviews)
- Price: $210 nightly, $240 total, Nov 18 - Nov 19, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!, by Carey D.

### [7\. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office](https://www.expedia.com/Greenport-Hotels-Blue-Bay-Dream.h89698399.Hotel-Information)

![A beach with people relaxing, a pier extending into the water, and a clear sky.](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698399/w906h683x59y0-97f670df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pipes Cove
- Guest rating: 10/10 (Exceptional, 35 reviews)
- Price: $305 nightly, $348 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: We had a great stay!! , by Callie E.

### [8\. Beach Block Hideaway](https://www.expedia.com/Greenport-Hotels-Beach-Block-Hideaway.h126648084.Hotel-Information)

![A wooden pathway leading to a beach with scattered rocks and greenery.](https://images.trvl-media.com/lodging/127000000/126650000/126648100/126648084/c8ae8d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pipes Cove
- Guest rating: 10/10 (Exceptional, 12 reviews)
- Price: $375 nightly, $428 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Beautiful 2 bedroom close to town. The house is well kept we would rent here again., by Teresa C.

### [9\. American Beech in Greenport - Petite King Room 7](https://www.expedia.com/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![An outdoor dining area with hanging lights, palm trees, and a bar.](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9.4/10 (Exceptional, 6 reviews)
- Price: $252 nightly, $288 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Great place! So nice., by Paul F.

### [10\. Steps to the beach | Seabreeze Cottage #3](https://www.expedia.com/Hampton-Bays-Hotels-Seabreeze-3-Cozy-Cottage-Just-25-Miles-To-US-Open.h114533130.Hotel-Information)

![A beach with footprints leading to the water, a sunset in the background, and a clear sky.](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/51264f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hampton Bays
- Guest rating: 6/10 (3 reviews)
- Price: $429 nightly, $454 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: "The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and..., by Lydia

### [11\. Northfork Townhouse walk to all](https://www.expedia.com/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

![A modern dining area with a wooden table, white chairs, and a chandelier.](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9.4/10 (Exceptional, 9 reviews)
- Price: $503 nightly, $574 total, Dec 1 - Dec 2, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again, by Beth R.

### [12\. Cozy Cottage by the beach - Seabreeze #1](https://www.expedia.com/Hampton-Bays-Hotels-Cozy-Cottage-By-The-Beach-Seabreeze-1.h137726748.Hotel-Information)

![A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.](https://images.trvl-media.com/lodging/138000000/137730000/137726800/137726748/45abc66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hampton Bays
- Price: $423 nightly, $448 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Southold vacation rentals

### [13\. Renovated Townhouse walk to all](https://www.expedia.com/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

![A modern kitchen with a marble island, pendant lights, and a patterned backsplash.](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/2f6846b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9.6/10 (Exceptional, 15 reviews)
- Price: $444 nightly, $507 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: The place was as advertised and in great walking distance to everything in town! , by Liz H.

### [14\. Beachfront Greenport Villa](https://www.expedia.com/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information)

![A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/28ef29e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 9.6/10 (Exceptional, 15 reviews)
- Price: $831 nightly, $949 total, Dec 1 - Dec 2, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Beautiful home, great views and host!, by Kate R.

### [15\. Charming Accommodations in the Hamptons](https://www.expedia.com/Sag-Harbor-Hotels-Charming-1-Bedroom-Apartment-With-AC-In-Sag-Harbor.h127427446.Hotel-Information)

![A patio with a wooden table and chairs, a door with a number, and a mailbox.](https://images.trvl-media.com/lodging/128000000/127430000/127427500/127427446/06cabd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Sag Harbor
- Price: $434 nightly, $496 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Southold vacation rentals

### [16\. 1-bedroom cottage with Grove Beach 🏖️ access.](https://www.expedia.com/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

![A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Clinton
- Guest rating: 9.8/10 (Exceptional, 67 reviews)
- Price: $222 nightly, $253 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!, by Marcy C.

### [17\. Beachfront Jacuzzi All Year - Black Swan Home](https://www.expedia.com/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-With-Jacuzzi-Year-Round.h92502496.Hotel-Information)

![A modern building with large windows overlooking a beach.](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8e05d72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hampton Bays
- Guest rating: 9.4/10 (Exceptional, 21 reviews)
- Price: $1,178 nightly, $1,243 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home., by John M.

### [18\. Windward Shores Ocean Resort](https://www.expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/f2542b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Napeague
- Guest rating: 8.8/10 (Excellent, 333 reviews)
- Price: $170 nightly, $194 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏, by Banessa

### [19\. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town](https://www.expedia.com/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information)

![A deck with outdoor furniture, a grill, and a potted plant.](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/992d88e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: $724 nightly, $827 total, Dec 1 - Dec 2, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!, by Jeannette M.

### [20\. Jacuzzi year-round - Villa Luz Private Home](https://www.expedia.com/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

![A house with a swimming pool, surrounded by trees and a fenced yard.](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/w733h550x122y0-0cadaa3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hampon Bays
- Guest rating: 9.6/10 (Exceptional, 27 reviews)
- Price: $1,085 nightly, $1,143 total, Nov 14 - Nov 15, Total with taxes and fees, for Our top choices for Southold vacation rentals
- Review: Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!, by Annie B.

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](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=183719&adults=2&sort=VACATION%5FRENTAL&openPlayBack=true)

## Find vacation rentals that suit your style

[Cottages](https://www.expedia.com/Hotel-Search?destination=Southold,%20New%20York,%20United%20States%20of%20America&regionId=183719&latLong=41.064823,-72.426193&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=COTTAGE)

[Apartments](https://www.expedia.com/Hotel-Search?destination=Southold,%20New%20York,%20United%20States%20of%20America&regionId=183719&latLong=41.064823,-72.426193&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=APARTMENT)

[Aparthotels](https://www.expedia.com/Hotel-Search?destination=Southold,%20New%20York,%20United%20States%20of%20America&regionId=183719&latLong=41.064823,-72.426193&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=APART%5FHOTEL)

[Condos](https://www.expedia.com/Hotel-Search?destination=Southold,%20New%20York,%20United%20States%20of%20America&regionId=183719&latLong=41.064823,-72.426193&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=CONDO)

[Houseboats](https://www.expedia.com/Hotel-Search?destination=Southold,%20New%20York,%20United%20States%20of%20America&regionId=183719&latLong=41.064823,-72.426193&adults=2&startDate=2026-11-20&d1=2026-11-20&endDate=2026-11-22&d2=2026-11-22&lodging=HOUSE%5FBOAT)

## Top Southold Hotel Reviews

### [The Shoals Suites and Slips](https://www.expedia.com/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Southold
- Review: The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing., by William, November 12, 2026, rated 10/10 Excellent

### [Silver Sands Motel & Beach Bungalows](https://www.expedia.com/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

![A beach with sun loungers and umbrellas, a sandy path, and a view of the water.](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/0f51f23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: We had a lovely stay., by Nicole, June 22, 2024, rated 10/10 Excellent

### [Zey Hotel](https://www.expedia.com/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![A two-story house with a covered patio, outdoor seating, and a well-maintained lawn.](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/5e616fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: It’s a nice hotel, it has a funky vibe to it and it’s very clean and the rooms are excellent. I definitely recommend it’s the perfect couple gate away hotel. Definitely coming back!!, by Jennifer, April 30, 2022, rated 10/10 Excellent

### [The Harbor Front Inn](https://www.expedia.com/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/27a70577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: everything was excellent. The only comment I would have is that the hallways smelled funny. Maybe if they could put a more fresh aroma and that’ll be great. Staff, everything was awesome., by Maureen, October 22, 2023, rated 10/10 Excellent

### [The Bentley Hotel Southampton](https://www.expedia.com/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Southampton
- Review: This is a super elevated motel vibe. Area is janky but accommodations were excellent., by Jennifer, April 30, 2025, rated 10/10 Excellent

### [House on Chase Creek](https://www.expedia.com/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information)

![A serene lakeside view with two Adirondack chairs facing the water, surrounded by autumn foliage.](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/efb81fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: The Heights
- Review: Beautiful view and excellent location. A short walk to the ferry to Greenport and a short drive to preserves. Owner more than accommodating. I will visit again., by Damon, March 8, 2022, rated 10/10 Excellent

### [The Chequit](https://www.expedia.com/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information)

![An outdoor patio area with string lights, tables, chairs, and a fire pit.](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/e8baba10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: The Heights
- Review: We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got., by Joseph, November 8, 2026, rated 10/10 Excellent

### [Cliffside Resort Condominiums](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 61475 Route 48 (North Road), Greenport, NY, 11944, US
- Location: Greenport
- Star rating: 3/5
- Guest rating: 9/10 (299 reviews)
- Review: We really enjoyed the room and the location. Our only criticism is that we were not able to access our room until 5:00 and we had to check out by 10 am in the morning. We basically lost at least half a day., by Jeannine, July 19, 2023, rated 10/10 Excellent

### [Sound View Greenport](https://www.expedia.com/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![A spacious room with wicker furniture, large windows, and a view of the sea.](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: Our stay was amazing! We had the best beach view! It was relaxing and one of the best getaways we’ve been on. If you want to connect to Netflix, HBO max, etc… bring a laptop or a console like Xbox, etc, bring a usb cord and wala you could connect. Thank you! We will be back!, by Marilyn, October 15, 2021, rated 10/10 Excellent

### [The Menhaden](https://www.expedia.com/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

![A two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/a4e7f774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: Quick anniversary night get away! Location was great, rooftop was amazing, and staff was super helpful! Made our stay special and memorable! Cant wait to go back for 2 nights!! Or more!, by Anonymous traveler, September 8, 2021, rated 10/10 Excellent

### [Sag Harbor Inn](https://www.expedia.com/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![A spacious hallway with a fireplace, a large window, and a built-in shelving unit.](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Sag Harbor
- Review: My stay was perfect. This family run hotel is outstanding, and great value for the money. Room (facing pool) was large, quiet and in perfect condition. Small private terrace with lounge chairs a big plus. Bathroom is large and modern with 5 star amenities (I appreciate that). Entire hotel feels like it was recently renovated. Will definitely stay here again!, by Anonymous traveler, April 30, 2021, rated 10/10 Excellent

### [American Beech Hotel](https://www.expedia.com/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information)

![A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Greenport
- Review: Great stay and service., by Jose, March 13, 2024, rated 10/10 Excellent

### [Faraway Sag Harbor](https://www.expedia.com/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information)

![A pool area with umbrellas, potted plants, and a pathway leading to a building.](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/823969b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Sag Harbor
- Review: Great location! On the bay but walking distance to town, by Victoria, April 30, 2025, rated 10/10 Excellent

### [Hyatt Place Long Island East End](https://www.expedia.com/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

![A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Riverhead
- Review: Hyatt Place East End was a very nice stay. Clean facilty, nice breakfast included, 2 pools. Would have like to see out door bar by the pool open., by Karen, August 18, 2024, rated 10/10 Excellent

### [The Hampton Maid](https://www.expedia.com/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information)

![A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hampton Bays
- Review: Such a beautiful property, lots of trees, lovely landscaping. They keep Crassula in pots on all of the porches as long as weather permits. The room I stayed in (double queen) was very spacious. Wood beamed ceiling with a ceiling fan, walk in shower. Loved the restaurant that was open for breakfast daily. Open for dinner Tuesday - Saturday while I was there. It's still family owned and run after 69 years. Great dining options all around, and lots to see and do on the island - although you..., by ALIX, October 3, 2024, rated 10/10 Excellent

### [The Captain Stannard](https://www.expedia.com/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information)

![A living room with a stone fireplace, grey sofas, and a coffee table.](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Westbrook Center
- Review: The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests., by Julie, May 27, 2024, rated 10/10 Excellent

### [The Preston House & Hotel](https://www.expedia.com/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![A two-story house with a front porch, a staircase, and a large glass window on the upper floor.](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Riverhead
- Review: Amazing staff and excellent rooms and facilities, by Leivona, November 7, 2023, rated 10/10 Excellent

## Find out more about Southold

### Everything you need to know about Southold vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southold vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southold vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

### Southold vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southold. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southold in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $194 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

### How to find incredible deals on Southold rentals

At Expedia, we put the best Southold vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southold vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## 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?

[WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly](https://www.expedia.com/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information): You might want to consider this vacation rental near Southold, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

### How many vacation rentals are there in Southold?

With 118 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.

## Explore a world of travel with Expedia

- [Lodging](?equalTargetTab=tab-0)
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- [Hotels near Sunset Beach](https://www.expedia.com/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
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- [Inns in Southold](https://www.expedia.com/Southold-Inns.d183719-aaInns.Travel-Guide-Accommodation)
- [Hampton Bays Hotels](https://www.expedia.com/Hampton-Bays-Hotels.d183681.Travel-Guide-Hotels)
- [Shelter Island Hotels](https://www.expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)
- [Hotels with Restaurants in Southold](https://www.expedia.com/Southold-Hotels-Hotels-With-Restaurants.0-0-d183719-tHotelswithRestaurants.Travel-Guide-Filter-Hotels)
- [East Hampton Hotels](https://www.expedia.com/East-Hampton-Hotels.d1524.Travel-Guide-Hotels)
- [Orient Hotels](https://www.expedia.com/Orient-Hotels.d6326191.Travel-Guide-Hotels)
- [B&B in Hamptons](https://www.expedia.com/Hamptons-Bed-And-Breakfast.d6056452-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [3 Star Hotels in Southold](https://www.expedia.com/3Star-Southold-Hotels.s30-0-d183719.Travel-Guide-Filter-Hotels)
- [Cutchogue Hotels](https://www.expedia.com/Cutchogue-Hotels.d183659.Travel-Guide-Hotels)
- [Motels in Southold](https://www.expedia.com/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
- [Montauk Hotels](https://www.expedia.com/Montauk-Hotels.d10637.Travel-Guide-Hotels)
- [Riverhead Hotels](https://www.expedia.com/Riverhead-Hotels.d5993.Travel-Guide-Hotels)
- [Beach Hotels in Southold](https://www.expedia.com/Southold-Hotels-Beach-Hotel.0-0-d183719-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Sag Harbor Hotels](https://www.expedia.com/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)
- [Farmstay in Southold Station](https://www.expedia.com/Southold-Station-Agritourism.d6186186-aaAgritourism.Travel-Guide-Accommodation)
- [Cottages in Southold](https://www.expedia.com/Southold-Cottages.d183719-aaCottages.Travel-Guide-Accommodation)
- [Greenport Hotels](https://www.expedia.com/Greenport-Hotels.d110728.Travel-Guide-Hotels)
- [Peconic Hotels](https://www.expedia.com/Peconic-Hotels.d144477.Travel-Guide-Hotels)
- [Pet-Friendly Hotels in Town of Southold Town](https://www.expedia.com/Destinations-In-Town-Of-Southold-Town-Pet-Friendly-Hotel.0-0-d553248635976002319-tPetfriendlyHotel.Hotel-Filter-Destinations)
- [B&B in Southold](https://www.expedia.com/Southold-Bed-And-Breakfast.d183719-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cheap Hotels in Southold](https://www.expedia.com/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
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- [Beach Hotels in Hamptons](https://www.expedia.com/Hamptons-Hotels-Beach-Hotel.0-0-d6056452-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Southold](https://www.expedia.com/Southold-Hotels-Luxury-Hotel.0-0-d183719-tLuxuryHotel.Travel-Guide-Filter-Hotels)
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- [Southold Hotels](https://www.expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)
- [Condo Rentals in Town of Southold Town](https://www.expedia.com/Town-Of-Southold-Town-Condos.d553248635976002319-aaCondos.Travel-Guide-Accommodation)
- [Hotels near Sparkling Pointe](https://www.expedia.com/Sparkling-Pointe-Hotels.0-l6327589-0.Travel-Guide-Filter-Hotels)
- [Beach Hotels in Greenport](https://www.expedia.com/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Flights to Hamptons](https://www.expedia.com/Cheap-Flights-To-Hamptons.d6056452.Travel-Guide-Flights)
- [Flights from East Hampton](https://www.expedia.com/lp/airports/hto/flights-from-east-hampton-airport)
- [Flights from Southold](https://www.expedia.com/lp/flights/183719/flights-from-southold)
- [Flights from MacArthur](https://www.expedia.com/lp/airports/isp/flights-from-macarthur-airport)
- [Flights to Southold](https://www.expedia.com/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)
- [Flights from Boston (BOS) to East Hampton (HTO)](https://www.expedia.com/lp/flights/bos/hto/boston-to-east-hampton)
- [Flights from New York (NYC) to East Hampton (HTO)](https://www.expedia.com/lp/flights/nyc/hto/new-york-to-east-hampton)
- [Flights from Francis S. Gabreski](https://www.expedia.com/lp/airports/fok/flights-from-francis-s-gabreski-airport)
- [Flights to East Hampton](https://www.expedia.com/Cheap-Flights-To-East-Hampton.d1524.Travel-Guide-Flights)
- [Flights from New York (JFK) to East Hampton (HTO)](https://www.expedia.com/lp/flights/jfk/hto/new-york-to-east-hampton)
- [Shinnecock Nation Cultural Center and Museum](https://www.expedia.com/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction)
- [Visit Hampton Bays](https://www.expedia.com/Hampton-Bays.dx183681)
- [Southold Vacations](https://www.expedia.com/Southold.d183719.Destination-Travel-Guides)
- [East Hampton Main Beach](https://www.expedia.com/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction)
- [The Old Field Vineyards](https://www.expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction)
- [Visit Greenport](https://www.expedia.com/Greenport.dx110728)
- [Visit Southold](https://www.expedia.com/Southold.dx183719)
- [Visit Southampton](https://www.expedia.com/Southampton.dx6782)
- [Visit Montauk](https://www.expedia.com/Montauk.dx10637)
- [Where to stay in Southold](https://www.expedia.com/Southold.dx183719.Where-To-Stay)
- [67 Steps Beach](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction)
- [Cooper's Beach](https://www.expedia.com/Coopers-Beach-Southampton.d6326842.Vacation-Attraction)
- [Visit Sag Harbor](https://www.expedia.com/Sag-Harbor.dx154327)
- [Car rental Southampton](https://www.expedia.com/Car-Rentals-In-Southampton.d6782.Car-Rental-Guide)
- [Car rental Southold](https://www.expedia.com/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)
- [Thrifty Car Rental Rental Cars in Southold](https://www.expedia.com/Thrifty-Car-Rental-Car-Rentals-In-Southold.d183719-c45.Car-Rental-Guide-Suppliers)
- [Click & Rent Rental Cars in Southold](https://www.expedia.com/Click-Rent-Car-Rentals-In-Southold.d183719-c1089.Car-Rental-Guide-Suppliers)
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- [Mattituck Vacation Rentals](https://www.expedia.com/Mattituck-Vacation-Rentals.d6223780.Travel-Guide-VacationRentals)
- [Bridgehampton Vacation Rentals](https://www.expedia.com/Bridgehampton-Vacation-Rentals.d6130684.Travel-Guide-VacationRentals)
- [Westhampton Beach Vacation Rentals](https://www.expedia.com/Westhampton-Beach-Vacation-Rentals.d6084385.Travel-Guide-VacationRentals)
- [Suffolk County Vacation Rentals](https://www.expedia.com/Destinations-In-Suffolk-County.d553248635083916458.Vacation-Rental-Destinations)
- [Peconic Vacation Rentals](https://www.expedia.com/Peconic-Vacation-Rentals.d144477.Travel-Guide-VacationRentals)
- [Riverhead Vacation Rentals](https://www.expedia.com/Riverhead-Vacation-Rentals.d5993.Travel-Guide-VacationRentals)
- [East Hampton Vacation Rentals](https://www.expedia.com/East-Hampton-Vacation-Rentals.d1524.Travel-Guide-VacationRentals)
- [Montauk Vacation Rentals](https://www.expedia.com/Montauk-Vacation-Rentals.d10637.Travel-Guide-VacationRentals)
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- [Water Mill Vacation Rentals](https://www.expedia.com/Water-Mill-Vacation-Rentals.d3000351347.Travel-Guide-VacationRentals)
- [Westhampton Vacation Rentals](https://www.expedia.com/Westhampton-Vacation-Rentals.d6140695.Travel-Guide-VacationRentals)
- [East Quogue Vacation Rentals](https://www.expedia.com/East-Quogue-Vacation-Rentals.d6125932.Travel-Guide-VacationRentals)
- [Noyack Vacation Rentals](https://www.expedia.com/Noyack-Vacation-Rentals.d6217344.Travel-Guide-VacationRentals)
- [Hamptons Vacation Rentals](https://www.expedia.com/Hamptons-Vacation-Rentals.d6056452.Travel-Guide-VacationRentals)
- [Greenport Vacation Rentals](https://www.expedia.com/Greenport-Vacation-Rentals.d110728.Travel-Guide-VacationRentals)
- [North Fork Vacation Rentals](https://www.expedia.com/North-Fork-Vacation-Rentals.d553248635074841663.Travel-Guide-VacationRentals)
- [Shelter Island Vacation Rentals](https://www.expedia.com/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)
- [Cutchogue Vacation Rentals](https://www.expedia.com/Cutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)
- [Hampton Bays Vacation Rentals](https://www.expedia.com/Hampton-Bays-Vacation-Rentals.d183681.Travel-Guide-VacationRentals)
- [Sag Harbor Vacation Rentals](https://www.expedia.com/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals)
- [Jamesport Vacation Rentals](https://www.expedia.com/Jamesport-Vacation-Rentals.d6323751.Travel-Guide-VacationRentals)
- [East Moriches Vacation Rentals](https://www.expedia.com/East-Moriches-Vacation-Rentals.d3000448461.Travel-Guide-VacationRentals)
- [Things to do in Hamptons](https://www.expedia.com/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities)
- [Things to do in Sag Harbor](https://www.expedia.com/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities)
- [Things to do in Southold](https://www.expedia.com/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)
- [Things to do in Shelter Island](https://www.expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)
- [Things to do in Southampton](https://www.expedia.com/Things-To-Do-In-Southampton.d6782.Travel-Guide-Activities)
- [Things to do in East Hampton](https://www.expedia.com/Things-To-Do-In-East-Hampton.d1524.Travel-Guide-Activities)
- [Things to do in Greenport](https://www.expedia.com/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)

## Other language versions

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