Pet-friendly holiday rentals in Southold

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Top-rated pet-friendly home rentals in Southold

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Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

3–10 Jan

$1,014 SGD per night

Guest favourite

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.

19–26 Sep

$1,191 SGD per night

Guest favourite

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!

8–15 Apr

$211 SGD per night

Guest favourite

Guest house in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

1–8 May

$483 SGD per night

Guest favourite

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.

11–18 Mar

$207 SGD per night

Guest favourite

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).

24–31 Mar

$230 SGD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

15–22 Oct

$952 SGD per night

Guest favourite

Holiday home in New London

5.0 out of 5 average rating, 117 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

Newly renovated in 2022-We’re excited to welcome you to our modern and cozy vacation home in a quiet community just a 5 minute walk to Ocean Beach! ~Special features~ • Dog-friendly! Fully fenced backyard • 2 BR w/Queen Tuft&Needle mattresses • Futon and couch both fold into add’l beds • Brand new in-unit washer/dryer • Gourmet kitchen; fully equipped & open concept island seating • Coffee bar w/complimentary K-cups • Gorgeous backyard & patio seating area w/firepit & charcoal grill

12–19 Nov

$282 SGD per night

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 101 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

13–20 Oct

$1,031 SGD per night

Guest favourite

Guest suite in Greenport

4.94 out of 5 average rating, 141 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

15–22 Feb

$502 SGD per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

12–19 Aug

$269 SGD per night

Guest favourite

Flat in Shelter Island Heights

4.91 out of 5 average rating, 227 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

14–21 Oct

$977 SGD per night