Holiday rentals with a kayak in New Haven

5 out of 5 average rating, 15 reviews

The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.

Home in Stratford

Cozy Winter Escape • Firepit • Near Train & I-95

*Inquiries welcome | longer stays 🍁 *Beautiful 3BR, 2BA home on the Housatonic River *Balcony w/ stunning water views * SHARED AMENITIES : driveway, yard, shed *Historic neighborhood near I-95 & Metro-North Railroad *20 min to Yale, UB, Fairfield U, & SHU *Near hospitals: Yale, BPT, ST. V’s *Perfect for groups & families * 1 hr to NYC *5 min drive to the beach *10 min drive to Hartford Healthcare Amphitheater & Webster Bank Arena *Lots of local breweries and restaurants to explore.

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.98 out of 5 average rating, 137 reviews

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.

4.92 out of 5 average rating, 106 reviews

A lakeside patio is depicted, featuring several metal chairs arranged around a firepit. Two swinging chairs hang from a pergola, while a dock with a boat and kayak is visible on the water. A vibrant American flag flutters in the background.

Guest suite in Newtown

waterfront on Lake Zoar[ SUITE]

Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

5 out of 5 average rating, 15 reviews

The exterior of a cottage is displayed, featuring a warm orange front door framed by a simple porch with steps leading up. The building's shingles are a natural brown, complemented by multiple windows that invite daylight. Lush greenery surrounds the entrance, enhancing the welcoming appearance.

Home in Branford

5 Star Branford Cozy Cottage

Quintessential beach cottage in Branford , Ct. Relax with the whole family at this 2025 newly renovated home with 4 bedrooms and 2000 square feet of living space. The home is located in the Indian Neck district of Branford within walking distance to Lenny's, The Stand & Little Riggs. 41 Soundview is 4 houses removed from the Long Island Sound and has beach rights. We promise to provide all the essentials you need for a comfortable. Pets welcome for $150 NYC - 75 miles New Haven - 10 mile

Flat in Downtown New Haven

A well-lit bedroom features a queen-sized bed adorned with a colorful quilt and a vibrant throw. Two bedside lamps provide soft illumination next to wooden nightstands. A desk with a chair is positioned near a window, and an air conditioning unit is visible, ensuring a comfortable environment.

4.95 out of 5 average rating, 96 reviews

Walk to Yale, Full Kitchen, Free Parking,Fast WiFi

In the heart of Yale, with self check-in and FREE PARKING! Queen-sized beds, a clean quilt, and quality pillows. Yale and downtown are walkable. Food trucks are around the corner on weekdays, and the best café in town is around the block with amazing coffee and food. The street is safe and protected by Yale security 24/7. Use the fast Wi-Fi, refrigerator, stove, coffee, TV, bikes, washer/dryer, A/C, etc. View my hundreds of 5-star reviews on other listings, and I look forward to hosting you!

4.97 out of 5 average rating, 109 reviews

A dining area features a wooden table surrounded by dark chairs, set with blue and white plates. Large windows allow natural light and provide an expansive view of the lake, where boats can be seen in the distance.

Cottage in Middlefield

Anchors' Away-

Anchors Away! Is the perfect setting for a quick get away! Or a prolonged vacation! Where reading, chilling, fishing, boating are not just words--Its a state of mind!! If you were any closer to the lake, you would feel as if you were on a houseboat... Every amenity is here for you to enjoy. Convenient to Interstate 91, Merrit Parkway, RT. 9.Recently gut renovated you will find the luxury of a hotel, yet quiet enjoyment. The property has two full bedrooms-one full bath-large great room!

4.97 out of 5 average rating, 35 reviews

A bright studio space is occupied by a spacious bed adorned with various green cushions. A kitchenette with modern appliances, including a microwave, is visible in the corner. Natural light filters through the windows, highlighting the decorative elements on the walls and floor.

Flat in Branford

Stony Crk Studio ideal for trvl nurses…

Peaceful shoreline studio/retreat ideal for trvl nurses and professionals—Single occupancy studio comprises upper east-wing of our home—has its own entrance up the exterior stairway with a dbbl-locked interior door and soundproofing for your privacy. Kick off your shoes and totally RELAX in our sleepy nook called Stony Creek, beach and boat harbor, food, shops and historic Thimble Islands. ALL within a 2 minute walk! See our guidebook for more information & tours and great ideas…

4.99 out of 5 average rating, 107 reviews

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

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.

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

5 out of 5 average rating, 116 reviews

Steps2Beach, Fish Pond, Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

4.95 out of 5 average rating, 124 reviews

Oceanfront Retreat with Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

4.94 out of 5 average rating, 282 reviews

A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.

Cottage in Guilford

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.

Cottage in Fairfield Beach

4.98 out of 5 average rating, 126 reviews

Charming Fairfield Beach Cottage

Escape to our newly renovated waterfront cottage in Fairfield, just steps from a private beach on the Long Island Sound. This charming retreat is perfect for families and couples, offering a modern kitchen, private deck, and high-speed WiFi. Unique perk: Enjoy complimentary 24/7 access to a beautiful co-working space just 3 miles away. A perfect blend of relaxation and productivity awaits!

Popular amenities for kayak rentals in New Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior of a newly constructed home features a combination of blue and white siding. Large windows are present on multiple levels, allowing for ample natural light. A staircase leads to the entrance, while parking is available beneath the house.

4.86 out of 5 average rating, 63 reviews

Newly Built Beach House Getaway

The three-story house features a light grey exterior with multiple balconies on the front. A double garage is located on the ground floor, with large windows above offering a view of the spacious balconies. The welcoming entrance is framed by well-maintained landscaping.

5 out of 5 average rating, 14 reviews

New build! 1 house from beach

4.9 out of 5 average rating, 31 reviews

A modern kitchen features a central island with three stools, surrounded by sleek countertops and essential appliances. Large windows and glass doors provide abundant natural light and a view of the outdoor area, seamlessly connecting the interior and exterior spaces.

Home in Clinton

Boulder Lake House Retreat

Superhost

A jetted spa is positioned under a wooden structure, surrounded by trees and offering views of the tranquil outdoors. Light reflects off the water's surface, creating a calming ambiance. Chairs are visible in the background, providing additional seating options.

Home in Newtown

4.78 out of 5 average rating, 23 reviews

Serenity by Lakefront Cottage!

5 out of 5 average rating, 27 reviews

A scenic waterfront terrace is framed by natural rock formations and lush greenery. An umbrella provides shade over a seating area featuring two Adirondack chairs and a small table, all offering unobstructed views of the water and boats in the distance.

Home in Guilford

Mulberry Seaside Cottage

4.96 out of 5 average rating, 55 reviews

A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.

Home in Morgan Point

Direct Beachfront Modern Cottage on Private Beach

4.88 out of 5 average rating, 24 reviews

A serene lakeside view features a well-maintained lawn leading to calm waters. Two comfortable yellow chairs are positioned on the grass, offering a perfect spot for relaxation. Trees frame the setting, while distant homes can be seen along the shoreline, enhancing the peaceful ambiance.

Home in Wolcott

Cozy Waterfront Lake House: 5 mins from ski slopes

4.9 out of 5 average rating, 59 reviews

Home in Madison

Coastal getaway with water views in every room

Cottage rentals with a kayak

4.93 out of 5 average rating, 55 reviews

A two-story cottage features horizontal siding and a distinctive light blue front door. A large window is positioned above the entrance, allowing natural light to enter. The garage is on the ground level, with a small staircase leading to the entryway.

Cottage in Milford

Salty Kisses Beach Cottage Milford CT

5 out of 5 average rating, 9 reviews

Rugged rocks line the shoreline, leading down to calm water. A wooden dock extends into the bay, providing access to the serene setting. Lush trees frame the scene, showcasing the natural beauty and tranquility of the coastal environment.

Cottage in Short Beach

Shore home in private community, away from it all

4.97 out of 5 average rating, 58 reviews

A serene view of an inlet bay beach is presented, featuring soft sandy shores leading to calm waters. A swan stands gracefully in the water, with the shoreline visible in the background, framed by trees and houses on the opposite side.

Cottage in Short Beach

Ret's Coastal Cottage w/Private Association beach

5 out of 5 average rating, 5 reviews

A beach cottage is presented with a wooden walkway leading from the sandy beach to the entrance. A deck with seating and a kayak is visible, with a backdrop of a clear blue sky and greenery completing the scene.

Cottage in Morgan Point

Caroline Beach Escape

Superhost

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

Cottage in Milford

4.87 out of 5 average rating, 90 reviews

Cheerful 3 Bedroom Cottage with Fire Place

4.77 out of 5 average rating, 60 reviews

The exterior of a beach cottage is depicted during twilight, with warm light glowing through the windows. The house features a white staircase leading to the entrance and is framed by bushes and decorative grasses. Nearby buildings share a similar coastal aesthetic.

Cottage in Milford

Beach cottage steps to Walnut Beach Historic CT

Other holiday rentals with a kayak

4.95 out of 5 average rating, 40 reviews

The living area features two comfortable, light-colored chairs positioned beside a small table. A large bay window allows ample natural light to fill the space, offering views of colorful foliage outside. Soft curtains frame the window, enhancing a welcoming environment.

Home in Fairfield

Once a Pond - time and stress slow down.

A serene view of a calm lake is captured, reflecting the scattered clouds above. Lush trees line the shore, creating a tranquil backdrop. The glassy water appears inviting, with gentle ripples enhancing the natural beauty of the scene.

Flat in Newtown

4.83 out of 5 average rating, 12 reviews

Spacious Lakeside Hideaway

5 out of 5 average rating, 24 reviews

The image shows a tranquil beach scene with a sandy shoreline. A family is seen walking along the water's edge, framed by lush greenery and blooming orange flowers in the foreground. Nearby, beach houses are visible, contributing to the peaceful atmosphere.

Home in Madison

Beach Home & Garden Paradise

4.87 out of 5 average rating, 30 reviews

Aerial view showcases a serene coastline lined with charming beachfront homes. The clear blue water reflects the sky, while the lush greenery in the background creates a peaceful backdrop. The image highlights the tranquil and inviting nature of the surrounding area.

Flat in East Shore

Cozy Beachfront Apartment - 6 min Yale/Downtown

A deck overlooking the Housatonic River features a circular table surrounded by four white chairs. A red umbrella stands upright, providing shade. The tranquil water reflects the greenery of the shoreline and the partly cloudy sky.

Bungalow in Seymour

4.7 out of 5 average rating, 140 reviews

Beautiful Waterfront on Housatonic River

4.93 out of 5 average rating, 30 reviews

A serene waterfront space features a wooden dock with two benches adorned with cushions. Lush greenery surrounds the calm waters, reflecting the clear blue sky and gentle landscape. The area invites relaxation and connection with nature.

Home in Fairfield Beach

Seaside Home - Walk to Beach & Marina

The cottage features a charming exterior with a white picket fence surrounding vibrant flower beds filled with colorful blooms. A porch adorned with screens offers a cozy space to relax. An American flag is mounted, adding to the inviting atmosphere of the home.

Home in Hotchkiss Grove

4.87 out of 5 average rating, 30 reviews

Walnut Lodge