
Vacation rentals with a kayak in Northwest Harbor
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Top-rated accommodations with a kayak in Northwest Harbor
Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

Wake up to Stunning Views at a Serene Waterfront Haven
This is a simple but lovely house with spectacular views of the water. Enjoy the sunset from the back patio or take kayaks out right off the dock. The comfortable living room has full length windows. There is also a guest cottage on the property that is ideal for extra space and privacy. Please know that there is a full size bedroom connected to the queen bedroom, there is a door but It is not entirely private since you have to walk through the queen bedroom to access the full bedroom.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge
[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Waterfront Joshua Cove Cottage with private beach.
Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Breezy Waterfront Home With private Dock
This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Beach Cottage | Steps to Water| Fireplace|Firepit
Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in August/September/October stays). Firepit area is shared with Bouy Cottage.

Cozy home. Comfy living
The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Serene East Hampton Escape - New Outdoor Sauna
A luxurious woodland escape with massive pool, outdoor dining living and play areas, fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

The Cottage at Indian Cove
A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Waterfront House on Fort Pond, MTK
Spacious house right on Fort Pond with relaxed bohemian vibe. Enjoy the open kitchen, reclaimed wood beams, and hand crafted furniture. Access directly to the water from the back yard. There are two other cottages that are two bedrooms each on property as well. We do live on the property full time and enjoy making our space a safe and clean environment.

Shelter Island 4 bed waterfront home with office
This waterfront spacious and sunny and bright home has four bedrooms, 2 living rooms, laundry room home office. It has 2 1/2 bathrooms. This home is perfect for a relaxing getaway in all seasons. It is located on Menantic Creek and 6 minutes from the ferry. Short term registration # 2025-v-0029
Popular amenities for Northwest Harbor kayak rentals
House rentals with a kayak

Renovated Ranch Home wPool & Beach Acces

5 Star Branford Cozy Cottage

Year Round Hamptons Waterfront

North Fork Sound Front Home with Pool

Magnificent Bayfront Retreat

Waterfront home with amazing views

Hang by the (Chel)SEA

Stunning sunset charming waterfront home 4 seasons
Cottage rentals with a kayak

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Caroline Beach Escape

Stunning waterfront modern farmhouse with dock.

The Bay Breeze

Ret's Coastal Cottage w/Private Association beach

Lovely 2 BR Beach House No. Shore

Prime location, walk to all, cozy cottage WHB

Renovated 2-Bedroom Cottage on the North Fork
Other vacation rentals with a kayak

Stony Crk Studio ideal for trvl nurses…

Garden Studio with private entrance

The Sandy Shack - Coastal Escape

Direct Beachfront Modern Cottage on Private Beach

Cottage by the beach

Coastal getaway with water views in every room

The Captain's Crib

1 Bedroom Hamptons Waterfront Cottage Rental
Quick stats about vacation rentals with a kayak in Northwest Harbor

Total vacation rentals
Explore 20 vacation rentals in Northwest Harbor

Nightly prices starting at
Northwest Harbor vacation rentals start at $346 CAD per night before taxes and fees

Verified guest reviews
Over 440 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Northwest Harbor vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Northwest Harbor rentals

4.9 Average rating
Northwest Harbor stays are highly rated by guests—averaging 4.9 out of 5!
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Southampton Beach
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