Holiday rentals with a kayak in New Haven

5* Branford Cottage with access to Owenego Club.

Quintessential coastal home in heart of Branford’s historic Indian Neck. Renovated in 2025, 4-bedroom, 2,000-sq-ft retreat blends 1920's charm w/modern comforts, & character of original fir hardwood floors throughout. It's 4 house's from the water, & access to Owenego Beach Club for guests. Walking distance to local fav's- Lenny's. Radici, Guacamloe's, & Lil Riggs. Modern amenities. Dog friendly under 50lb - $150 per dog per stay(max 2), undisclosed dogs incur add'l fine. See add'l guidelines.

Outdoor spaces · Value · Heating

Historic Riverside Getaway|Private Beach + Boats

Newly renovated riverfront home circa 1885 - direct access and private beach on the Quinnipiac River 3 bedrooms, 2.5 baths, double sinks & steam shower in primary bathroom High cleaning standards Private Waterfront access - watercraft available to rent on property BBQ/outdoor entertainment area Open concept main floor: 4K Roku Smart TV, complete with state of the art speakers, 2 couches, 1 full sized pull-out bed High-end kitchen appliances including: double dishwasher, full sized gas range/oven

Hospitality

Walnut Beach Escape Fenced Oasis Yard

🌊 Steps from Walnut Beach & Silver Sands State Park, this guest-favorite coastal escape blends beach access, privacy & relaxed luxury. Enjoy a tropical-inspired backyard oasis with a cascading fish pond, multiple lounge areas & a seasonal palm tree—perfect after a day by the shore. Inside, unwind in a beautifully designed home with a gourmet kitchen & modern comforts. Just 90 minutes from NYC & 15 from New Haven, it’s an ideal retreat for beach days, nature lovers & laid-back coastal living.

Value · Location · Check-in

Anchors' Away-

Escape to a charming lakefront retreat where peaceful mornings, panoramic water views, are the gift that nature gives you. conveniently located near major highways, shopping, restaurants and local attractions, - Our cottage offers the best of two worlds-tranquil relaxation and easy access to everything you need. Guests will be given a Hold Harmless Agreement to sign upon reservation acceptance-There are kayaks available to use- A waiver has to be signed before they can be used on the lake

Outdoor spaces · Value · Parks

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Location · Outdoor spaces · Access

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

Outdoor spaces · Location · Air conditioning

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until mid-March)

Outdoor spaces · Location · View

Ret's Coastal Cottage w/Private Association beach

A charming sun filled cottage, 500 ft (2 min walk) to a sandy inlet bay beach, nestled in the quaint Short Beach community of Branford. The cottage offers a large open floor plan, wood burning fireplace, all the space & coziness you need! Perfect place to relax but close enough to go out and experience all things New England has to offer. Explore Long Island Sound, on kayaks or biking, both provided, take walks or jog along the beautiful scenic area. Walking distance to 2 great restaurants.

Value · Location · Quiet

Mulberry Seaside Cottage

Enjoy direct water views any time of year in this cozy cottage. Relax on the generous porch swing, eat dinner overlooking the water, watch the sunset on the secret waterfront terrace, and stay active kayaking, biking, and swimming. The large backyard is great for yard games. In the cooler months, cozy up to the outdoor gas fire or inside with a book while watching a stunning winter sunset over the water. Minutes to the charming Guilford green, restaurants, Yale University and train station.

Outdoor spaces · Location · Indoor spaces

Riverfront Antique Cabin in the Heart of Madison

Antique, rustic cabin on Neck River just minutes from downtown Madison. Come kayak, birdwatch, and relax. First floor has a full, eat-in kitchen and tranquil living room with TV, pingpong, and games. Walk (1.5 miles) or kayak (during high tide) to Grass Island for a tranquil beach experience, or drive (2 miles) to downtown, with beaches, bookstores, a quaint town cinema and a wide array of restaurants. Relax (or fish) on the stone porch as egrets, osprey, and kingfishers fly above you.

Outdoor spaces · Value · Air conditioning

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

Value · Outdoor spaces · Hiking

Luxe cozy 2br/1ba Milford bungalow-walk to beach!

Beautifully updated bungalow 3 minute walk to beach. Features two decks for views & enjoyment of Silver Sands State Park. Back deck has dining table & grill for dinners, drinks, birdwatching, stargazing. House has cedar outdoor shower, two double kayaks, stand up paddle board, paddles, beach chairs/towels, umbrellas, cooler, wagon. Spacious living room has tons of natural light. Bedrooms are cozy each with a full bed; primary opens to back deck. 5 min drive to downtown Milford.

Location · Value · Cleanliness