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House vacation rentals in Southold

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Top-rated house rentals in Southold

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

Mar 31 – Apr 7

G$107,899 GYD per night

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Sep 19 – 26

G$183,050 GYD per night

Home in East Haven

4.88 out of 5 average rating, 196 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Apr 8 – 15

G$32,467 GYD per night

Home in Southold

5.0 out of 5 average rating, 16 reviews

Le Petit Cottage Southold NY

Experience the charm of a two-bedroom cottage in Southold, New York. Enjoy easy access to nearby South Harbor Park Beach, where you can swim and soak up the sun. Immerse yourself in the local wine scene with wineries just a short distance away. Explore nearby farms to savor fresh produce and artisanal goods. Unwind on the outdoor deck in the fresh North Fork air after a day of swimming, wine tasting and farm visits. Greenport and Shelter Island Ferry are a short ten minute drive away.

Nov 7 – 14

G$46,504 GYD per night

Home in East Lyme

4.96 out of 5 average rating, 105 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Mar 11 – 18

G$31,757 GYD per night

Home in Holbrook

4.91 out of 5 average rating, 237 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Jul 20 – 27

G$22,609 GYD per night

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Feb 16 – 23

G$25,474 GYD per night

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

Apr 19 – 26

G$99,062 GYD per night

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Jan 9 – 16

G$173,654 GYD per night

Home in Greenport

4.97 out of 5 average rating, 221 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Aug 9 – 16

G$119,082 GYD per night

Home in Greenport

4.98 out of 5 average rating, 144 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

May 10 – 17

G$160,492 GYD per night

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

Sep 4 – 11

G$119,759 GYD per night

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Popular amenities for Southold house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Shelter Island

4.97 out of 5 average rating, 194 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Feb 6 – 13

G$205,464 GYD per night

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct 3 – 10

G$120,357 GYD per night

Home in East Hampton

4.93 out of 5 average rating, 140 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Sep 30 – Oct 7

G$191,827 GYD per night

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Oct 25 – Nov 1

G$111,552 GYD per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Oct 3 – 10

G$190,757 GYD per night

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Nov 16 – 23

G$203,975 GYD per night

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Oct 23 – 30

G$144,503 GYD per night

Home in Southampton

4.96 out of 5 average rating, 130 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Jun 7 – 14

G$228,294 GYD per night

Weekly house rentals

Home in East Marion

4.83 out of 5 average rating, 6 reviews

Private North Fork Cottage- Walk to Beach!

Nov 6 – 13

G$50,055 GYD per night

Home in Cutchogue

4.97 out of 5 average rating, 30 reviews

Cozy Cottage with Views

Dec 24 – 31

G$66,030 GYD per night

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

G$137,795 GYD per night

Home in Southold

4.96 out of 5 average rating, 28 reviews

Bright Oasis in Beautiful North Fork Wine Country

Jan 18 – 25

G$113,660 GYD per night

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Dec 5 – 12

G$90,315 GYD per night

Home in Southold

5.0 out of 5 average rating, 31 reviews

Salt & Sea House - Near wineries, farms, & beaches

Sep 14 – 21

G$98,125 GYD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Sep 29 – Oct 6

G$103,145 GYD per night

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Nov 18 – 25

G$115,028 GYD per night

Private house rentals

Home in Southold

4.97 out of 5 average rating, 35 reviews

Water & Vineyard views, 4 bedrooms

Jan 3 – 10

G$215,806 GYD per night

Home in Southold

5.0 out of 5 average rating, 19 reviews

Horton House

Nov 2 – 9

G$64,226 GYD per night

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

May 16 – 23

G$180,313 GYD per night

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

Oct 4 – 11

G$118,930 GYD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Dec 29 – Jan 5

G$136,814 GYD per night

Home in Greenport

4.96 out of 5 average rating, 25 reviews

Water front 3 bedrooms 2 bathrooms beach house

Nov 4 – 11

G$160,873 GYD per night

Home in Southold

4.93 out of 5 average rating, 15 reviews

Farm house with vineyard views

Nov 11 – 18

G$47,157 GYD per night

Home in Mattituck

5.0 out of 5 average rating, 30 reviews

Immaculate NOFO Beach House Steps from Beach

Nov 5 – 12

G$156,018 GYD per night

Quick stats about house rentals in Southold

Total rentals
170 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
G$20,920 GYD before taxes and fees

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