Vacation rentals with a kayak in Westmoreland County

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Popular amenities for Westmoreland County kayak rentals

House rentals with a kayak

Guest favorite
An aerial view captures a charming single-story home nestled among lush greenery, with a panoramic view of Mattox Creek extending to the Potomac. The well-maintained landscaping and surrounding trees create a peaceful setting, highlighting the home's proximity to the water.
Home in Colonial Beach
4.89 out of 5 average rating, 55 reviews

Waterfront Home w/ Private Dock!

PennieRating, 5 stars3 weeks ago
Mari was so responsive and helpful. The house has everything you could possibly need and the beds were so comfortable! Thank you Mari!
Top guest favorite
A wooden dock extends into calm waters, featuring two boats secured at the end. A colorful sail with bright red, yellow, and blue stripes stands upright, contrasting with the clear blue sky. Surrounding greenery creates a serene backdrop.
Home in Montross
4.96 out of 5 average rating, 46 reviews

Game-Themed Water Fun! Boats+Pool+Beach+King Bed

AlishaRating, 5 stars1 week ago
Absolutely beautiful stay! The cabin has the cutest theme and the proximity to the water was great and a gorgeous view. Abby and family was so kind, responsive, and great hosts. Would highly recommend this getaway!
Top guest favorite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island
4.99 out of 5 average rating, 94 reviews

Waterfront 4-BR home w/ hot tub & charging station

AndreeRating, 5 stars2 days ago
We had an extraordinary family time in Jen's house. Cobb island is an unexpected gem. Being on the Neal Sound of the Island was best for birding and kayaking. A magical week everybody will remember! Thank you to Jen for providing such a great place!
Top guest favorite
Home in Colonial Beach
4.98 out of 5 average rating, 65 reviews

Serene, well-appointed waterfront retreat

ErinRating, 5 stars3 weeks ago
This house and the amenities are amazing. It was perfect for our family reunion with 5 couples. Enough room for everyone to have space. My favorite part was gathering around the round dinner table with the 10 of us. We also took the kayaks out and up Mattox creek for a wonderful morning of a peaceful paddle. The Lodge was perfect for my husband and I to step away from the group and have some privacy. I highly recommend!!
Guest favorite
A bright orange kayak is positioned on the sandy shore near a dock, framed by gentle waves of the water reflecting a colorful sunset. The sky displays shades of pink and purple, while soft clouds are illuminated by the setting sun.
Home in Leonardtown
4.96 out of 5 average rating, 68 reviews

The River House: A private waterfront oasis…

ChrisRating, 5 stars1 week ago
What can we say? John's property was everything we hoped it would be. The back yard is full of fun yet also serene and peaceful. The water is perfect for floating in a tube, kayaking, or just wading in and cooling off. The house has everything anyone could want. As an added bonus, you'll enjoy watching an Osprey family, Herons, Ducks, Mockingbirds, Blue Jays, Cardinals, and even some Minks and a Groundhog. The firepit is perfectly placed by the water for a morning fire as the mist rises, and especially in the evening for spectacular sunsets over the bay. Even getting there is a joy, as you go down a quiet country road lined with beautiful farms, quaint churches, and plenty of deer and wildlife. If your looking for a tourest trap vacation, then Leonardtown is not for you. But if you want a quiet getaway with all the amenities, then this is your place!
Guest favorite
A living area is displayed with a comfortable brown sofa and two light-colored armchairs facing large windows that provide a view of the Potomac River. A wooden coffee table sits in the center, accompanied by a decorative rug and neutral wall art.
Home in Colonial Beach
4.98 out of 5 average rating, 63 reviews

Waterfront Paradise with own Beach, Kayak, & Grill

JulianaRating, 5 stars3 weeks ago
Lulus place was beautiful and a wonderful way to spend the weekend! Just as described, and the private beach front was lovely
Superhost
A two-story house with a light-colored exterior and a spacious front porch is set against a clear blue sky. Lush green grass surrounds the property, with trees flanking the sides, creating a serene and open atmosphere.
Home in Avenue
4.88 out of 5 average rating, 17 reviews

Private Getaway at Four Waters

AshleyRating, 5 stars3 weeks ago
Perfect place for a girl's weekend bachelorette trip! We kept joking that we felt like we were in Bridgeton. We loved the decor and spacious rooms which are perfect for cozy late-night chats! The hot tub and porches were wonderful for taking in the gorgeous views of the river. We loved sitting and watching the swans, deer, and otter. Brooke and her husband were kind and welcoming; truly wonderful hosts who went above and beyond for us to make sure we had a great time! We left the weekend feeling relaxed and refreshed, and we're already ready to come back for more! Thanks again!
Guest favorite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross
4.96 out of 5 average rating, 76 reviews

Waterfront home, private dock

ShufanRating, 5 stars3 weeks ago
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.

Cottage rentals with a kayak

Top guest favorite
The cottage features a striking red metal roof contrasting against the greenery of the landscape. Surrounded by the water, the property includes a well-maintained lawn with trees and shrubs. The structure showcases a charming design with a welcoming entrance and outdoor steps leading to the main door.
Cottage in Lancaster
4.94 out of 5 average rating, 34 reviews

Waterfront Cottage with Beautiful Sunset Views

DavidRating, 5 stars1 week ago
This was an amazing trip. We are going to make this a yearly trip. It was private and peaceful. It stormed a little bit but that was nice to watch out of the bedroom upstairs or on the screened in porches. We both really enjoyed the house!
Guest favorite
An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.
Cottage in Heathsville
4.87 out of 5 average rating, 114 reviews

Cottage with a view!

HollyRating, 5 stars1 week ago
We came to relax and it was successful. A cute little cottage by the river.
Superhost
A covered deck offers seating with wicker chairs and colorful cushions overlooking the calm waters of the Chesapeake Bay. The decking is made of warm-colored wood, and a gentle view of the shoreline can be seen in the distance, enhancing the serene atmosphere.
Cottage in Reedville
4.88 out of 5 average rating, 211 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

TheresaRating, 5 stars3 days ago
If you are looking for a beautiful and peaceful location to unwind, this is a great place! The home is very comfortable and has everything you could need. But the highlight was the amazing views of the bay from practically every window in the house. We would definitely recommend staying here!
Superhost
A remodeled cottage is set amidst a green lawn, featuring a spacious screened front porch and surrounded by trees. The building showcases a classic design with a dark exterior and a contrasting light roof, under a clear blue sky.
Cottage in Warsaw
4.93 out of 5 average rating, 120 reviews

Modern 2 Bdrm Cottage in Historic River Community

C. CaliRating, 5 stars3 weeks ago
Loved staying at this quiet retreat! Mornings listening to birds, afternoons in the sunny backyard, stars and stars! Really loved this place and will be back again.
Top guest favorite
A waterfront cottage is set against a backdrop of lush greenery, with a stone wall bordering the water. The well-maintained lawn extends towards the river, and the cottage features a covered patio, inviting outdoor seating, and a surrounding cluster of trees.
Cottage in Cobb Island
4.97 out of 5 average rating, 62 reviews

Where Eagles Soar *Stunning Waterfront Views*

NancyRating, 5 stars2 weeks ago
My friends and I immediately felt relaxed and cared for in this delightful home. We loved that it was right on the water and that we could enjoy seeing the Potomac River from so many rooms. The beds were very comfortable. Sue is a thoughtful and very pleasant host. We enjoyed our stay very much.
Top guest favorite
Cottage in Tall Timbers
5 out of 5 average rating, 47 reviews

Charming Waterfront Cottage with Sunset Views

LeslieRating, 5 stars3 weeks ago
We had an amazing holiday weekend at Dave and Jenny’s cottage! They were always so quick to respond with any requests we had! The cottage as perfect and just like the pictures. They literally had thought of everything! The sunsets were absolutely stunning and it was truly the most relaxing time we’d had in a while! It was just what we needed !
Guest favorite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross
4.93 out of 5 average rating, 95 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

AmandaRating, 5 stars1 week ago
This lake house was such a relaxing place to stay! Had everything we needed and then some. It’s a bit of a hill to climb to get back to the house from the lake but not terrible. The beach recommendations were great! We found a ton of shark teeth and the kids really enjoyed themselves.
Top guest favorite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown
4.96 out of 5 average rating, 95 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

WendyRating, 5 stars3 days ago
I think this is my 5th time staying there. Always thinking of my return visit before even leaving!

Cabin rentals with a kayak

Superhost
A sunlit deck extends alongside the cottage, featuring smooth wooden planks. Two chairs and a small table are positioned invitingly near the edge, with tall trees providing shade and a view of the bay beyond.
Cabin in Reedville
4.74 out of 5 average rating, 23 reviews

"Elderberries" Chesapeake Bayfront Cottage

JoelRating, 5 stars1 month ago
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.
Superhost
A log cabin with a rustic exterior is surrounded by lush greenery. The wraparound porch features a wooden railing and an American flag hangs proudly. A detached garage is visible in the background, and the property is set against a peaceful lake.
Cabin in Lancaster
4.9 out of 5 average rating, 58 reviews

Riverside R&R: Cabin, Dock, Kayak & Game Arcade

LisaRating, 5 stars1 week ago
We are two families that met up for a relaxing getaway after celebrating a high school graduation. This was the perfect place. The downstairs had lots of games and a big screen for them to hook their switch up to. We watched movies upstairs. And use the well-equipped kitchen each night to make a big dinner. The kids took the kayaks and canoe out one afternoon as well. Although I would say they definitely wouldn’t swim there. Compass entertainment complex is very close and they enjoyed their time there. We also went to a movie there one night. It is a beautiful home in a peaceful setting. Especially down on the dock at night. It was very quiet. We would definitely recommend this home.
Cabin in Lancaster
5 out of 5 average rating, 5 reviews

Waterfront Lancaster Cabin ~ 10 Mi to Kilmarnock!

MarthaRating, 5 stars10 months ago
We piled 5 adults and a toddler into the house on Kelley Neck Drive, and it worked just fine! Bathrooms, AC, kitchen, appliances, etc, all worked perfectly, the furniture was comfortable and in good shape, and the house was spacious. The yard was perfect for us, but might have been small for older kids, and I wish there had been more than one kayak (but even one kayak was a bonus!) The heron was fishing at the mouth of the our private lagoon every morning, and an osprey and eagle visited as well. We barely heard any neighbors, and the nights were quiet and peaceful. Thank you!
Guest favorite
An aerial view showcases the property surrounded by tall trees, with a clear path leading to a waterfront area. The serene water reflects the sunlight, while the landscape features a mix of greenery and open space, highlighting the tranquility of the setting.
Cabin in Ridge
4.95 out of 5 average rating, 65 reviews

Pizza Friday

LoisRating, 5 stars3 weeks ago
Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.
Guest favorite
A wooden dock extends over calm waters, featuring two parked kayaks in vibrant colors. Sunlight filters through surrounding trees, illuminating two foldable chairs positioned on the dock, creating an inviting spot for relaxation by the water.
Cabin in Lusby
4.9 out of 5 average rating, 268 reviews

Peaceful Waterfront Retreat on The Bay

LydiaRating, 5 stars4 days ago
Incredible space! Devin’s place on the water has everything you need. It would be tight with more than two adults but it worked great for us and our small dog.
Guest favorite
A wooden dock extends into calm waters, framed by lush greenery. Two kayaks are secured to the side of the dock, and an expansive sky filled with soft clouds reflects over the serene surface of the creek, creating a peaceful outdoor scene.
Cabin in Lusby
4.93 out of 5 average rating, 204 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

EricRating, 5 stars2 weeks ago
My stay was exactly what i needed it to be. It was a quick 90 minute drive from the city, but once I got there I found exactly what I needed. 2 days of peace, quiet, and seclusion. I had to make a quick run, to the grocery store, but it was convenient and people were really nice. Next time I come, I’ll probably explore the Solomon Islands.
Guest favorite
A charming black exterior cottage is surrounded by autumn foliage, featuring a welcoming front porch with steps leading to the entrance. Flower boxes adorn the windows, while a small deck is visible to one side, adding to the inviting outdoor space.
Cabin in Montross
4.96 out of 5 average rating, 25 reviews

Camp Heron : Waterfront Cabin on the Potomac

CrystalRating, 5 stars3 weeks ago
This Airbnb truly felt like staying in someone's home. There were lots of items provided in the house -- from toys in the cabinets, to records to listen to and the kitchen was very well stocked with pans, plates and seasonings. Outside we loved using the crab pots (though we came up empty and didnt catch any crabs) and lighting a fire at the fire pit at night.
Top guest favorite
A serene lakeside view features a wooden dock extending into the calm water, flanked by greenery. Two kayaks are displayed on a rack, while a fire pit with seating is positioned nearby. A safety notice is visible, ensuring guest awareness.
Cabin in Lusby
4.98 out of 5 average rating, 90 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

LaurenRating, 5 stars3 weeks ago
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

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