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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!

Dec 19 – 26

€ 572 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.

May 31 – Jun 7

€ 839 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

€ 166 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.

Dec 2 – 9

€ 237 per night

Home in Brookhaven

4.95 out of 5 average rating, 127 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

Mar 23 – 30

€ 173 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).

Jan 15 – 22

€ 129 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 14 – 21

€ 466 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.

Feb 4 – 11

€ 851 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 10 – 17

€ 559 per night

Home in Cutchogue

4.96 out of 5 average rating, 74 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea.

Oct 29 – Nov 5

€ 298 per night

Home in Greenport

4.98 out of 5 average rating, 143 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

€ 758 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

€ 561 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 East Hampton

4.93 out of 5 average rating, 140 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Feb 11 – 18

€ 354 per night

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct 2 – 9

€ 609 per night

Home in Southampton

4.96 out of 5 average rating, 130 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Mar 12 – 19

€ 381 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

€ 537 per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Dec 21 – 28

€ 900 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

€ 692 per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Oct 24 – 31

€ 301 per night

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

Dec 4 – 11

€ 525 per night

Weekly house rentals

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

€ 656 per night

Home in Cutchogue

4.97 out of 5 average rating, 30 reviews

Cozy Cottage with Views

Dec 24 – 31

€ 324 per night

Home in Southold

4.96 out of 5 average rating, 27 reviews

Bright Oasis in Beautiful North Fork Wine Country

Jan 24 – 31

€ 594 per night

Home in Southold

5.0 out of 5 average rating, 31 reviews

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

Jun 4 – 11

€ 442 per night

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Dec 17 – 24

€ 427 per night

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Jan 6 – 13

€ 538 per night

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

Feb 16 – 23

€ 578 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

€ 766 per night

Private house rentals

Home in Southold

4.93 out of 5 average rating, 15 reviews

Farm house with vineyard views

Apr 21 – 28

€ 240 per night

Home in Southold

5.0 out of 5 average rating, 19 reviews

Horton House

Nov 2 – 9

€ 317 per night

Home in Greenport

5.0 out of 5 average rating, 70 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

€ 483 per night

Home in Mattituck

5.0 out of 5 average rating, 30 reviews

Immaculate NOFO Beach House Steps from Beach

Nov 5 – 12

€ 731 per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Jun 3 – 10

€ 507 per night

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

Dec 18 – 25

€ 459 per night

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

Apr 4 – 11

€ 604 per night

Home in Mattituck

4.92 out of 5 average rating, 61 reviews

Walk to Breakwater Beach in Heart of Wine Country

Mar 3 – 10

€ 509 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
€ 93 before taxes and fees

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