
Holiday rentals with outdoor seating in Jamestown
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Jamestown
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for outdoor seating rentals in Jamestown
House rentals with outdoor seating

Bluegrass Gables: Lake Cumberland Cottage
The home is beautiful! Very spacious and very peaceful, super easy to find. The host was very kind and quickly responsive to any inquiries I had. We had an amazing weekend stay here and would def go back đ

Welcome to your Dream Lake Home
We had such an amazing stay at Samathaâs! She was so friendly and accommodating. She worked around all of our needs since we came out of state, we had a blast! The view was also breathtaking!

Avery Acres
This is our favorite place to stay. The address is nice. The house is clean. The host is super! We'll be back!

Ina's Place
Excellent stay. Met all our needs and then some. Only regret is that we didnât stay long enough. We were in town for a wedding. Wish we had planned a longer stay. Very comfortable home that managed our multigenerational family (including small children) extremely well.

Home 0.2 miles from boat ramp with game room
Great place to stay with a detached garage with activities to do in the garage. Very responsive to any questions we had. Worked with us without question when our plans unexpectedly changed. Definitely a great place to stay with easy access to the lake! Highly recommend this property!!!!

Waterfalls, fishing pond, lake view, and 8 acres!
Justinâs place is perfect for the family looking for a quiet, comfortable, and secluded getaway. He insured all the little amenities were available, staying in touch to see if anything was needed. Just a great host with a wonderful place for others to enjoy. Highly recommend

4 bed 2 bath by Jamestown Marina
This is a perfect space for my family of 5. Hosts were great and responded when I had questions. Love the patio and black-stone grill for group meals. Weâve stayed here twice now and will definitely be back!

Lake Cumberland Getaway near Conley & Burnside
5 stars ALL the WAY! These folks do Air BNB the old fashioned way, before it became just another business. They have thought of everything and go above and beyond to make their guests feel welcome and cared for. We were visiting family and were thrilled to be able to cook a full meal and have everything we needed. They also thoughtfully provided snacks and s'more fixings. They even went so far as to lay a fire in the fire pit that just needed to be lit! This was a peaceful slice of heaven!
Apartment rentals with outdoor seating

New near Jamestown Dock - B
This was a great place to stay very convenient to the lake boat ramps, and a very good parking lot for turning and parking boat trailer with truck

Cozy in Kentucky
These accommodations were just what we were hoping for! Our stay was very comfortable and was located in a quiet neighborhood. We had privacy and everything that we needed to make our stay an excellent one! Sitting on the deck and watching the sunset was an extra and unexpected treat! It is obvious that the host has thought of everything to make her guests comfortable and welcome! I would recommend this Airbnb to anyone. It was an added bonus that it is less than 2 miles from the local marina on Lake Cumberland. We were so pleased with our choice!

Spacious cozy beautiful getaway.
Thanks for hosting us u have a great place and it fits our needs

Resort Clubhouse
My family really enjoyed the space for our trip to the lake. The hosts accommodated space for our boat when we asked. It was so close to a great boat ramp, we were at the lake in less than 4 minutes. My kids really enjoyed the heated indoor pool after a day at the lake. We actually really enjoyed being in the RV park where there were other kids to play with and it was so quiet and peaceful. The hosts stopped by while we were sitting on the porch to make sure we didnât need anything. The bedrooms had plenty of space. No complaints, such a great space we will very likely book again in the future! Thank you for having us!

Woodson Bend Resort getaway on Lake Cumberland.
Christopherâs place at Woodson Bend Resort provided all that was necessary for a wonderful family stay the first week of August. The weather was beautiful and so we enjoyed the comfortable and well-appointed back porch; the walks to the pool; the dry-accommodating and nicely-decorated living spaces; and, the closeness in proximity to the pickleball courts. After our days on the boat, we were grateful for the ample kitchen space, cookware, utensils, and kitchen linens to enjoy family meals around the table! The location of this unit is excellent - easy to reach the Pro Shop, pool, restaurant, playground, volleyball court and pickleball courts. We did not use the outdoor fire pit, but noticed the stock of wood and great arrangement of outdoor chairs that would make this a very lovely space to enjoy. Would highly recommend Christopherâs place in Woodson Bend!

The Ivan House
Joe was a very responsive host. He made sure to check in with me to see if I needed anything. His place was so peaceful! I have trouble sleeping in new places but I had the best sleep there!! There was a Christmas tree, lovely candles, lots of extra blankets. It was truly my home away from home. Thank you Joe!

Beauty on the 7th Fairway (65-3) Golf Pool Tennis
My family loved staying at this condo in Woodson Bend. The unit itself was extremely clean. The appliances appeared brand new and worked well. We loved the screened in porch and saw multiple deer right outside our porch every day. The televisions in the units had all of the major streaming services installed, which was great for my kids to enjoy movies and tv shows in the evenings. We were able to walk to the front of the resort to enjoy the pool and playground, both of which were clean and nicely maintained. My husband, dad, and brother in law enjoyed the golf course. The restaurant at the resort is delicious as well. It is BYOB, which isnât a bad deal as long as you have plenty of what you like to drink in your condo. Only two drawbacks to this unit-the sheets on the beds are not the softest and the bunk room is very small with no windows. Neither of these were dealbreakers for us and we would definitely stay in the unit again! The bunk room is probably better for kids than adults.

The Rustic Suite (500A)Fun, Lake, Golf carts, Food
This place was spotless, comfortable and peaceful! I hope to return this summer.
Apartment rentals with outdoor seating

Woodson Bend Gorgeous Lake View Condo First Floor
Woodson Bend is always a great place to be. We love the pool, ability to put your own boat in the water at the resort, the golf and the golf cart community. Debbieâs place is clean, well stocked and as it is shown in the pictures and description.

Amen Corner at Woodson (46-3) Golf Pool Pickleball
Great Location. Great place. Dianna was very responsive and trip was good.

Green Lite Lakeview (105-1) Lake, Golf, Pool
I had a wonderful stay! The community here is truly beautiful, with a warm and welcoming atmosphere that immediately made me feel at home. The host was fantasticâattentive, friendly, and always ready to help with anything I needed. Every detail was thoughtfully taken care of, ensuring that I had exactly what I was looking for during my visit. I couldnât have asked for a better experience, and I would gladly stay here again in a heartbeat.

Lake Cumberland Resort Condo w/ Direct Lake Access
Wendy was a great host. We frequent Woodson bend and I will be saving her place as an option in the future. Walk to the pool in less than 5 minutes. The beds were comfortable. Kitchen is fully stocked with everything. You will need to purchase ice as the fridge did not make any, not a big deal since you can get a bag at the guard shack for a few bucks. The only thing I will mention is that I believe owner has a dog so if you have allergies, be mindful of this. My wife dealt with allergies during our stay so she avoided the living room and took Benadryl to help. We were gone most of the day at the pool or on the lake. Overall, nice and peaceful, would recommend.

Lakefront Condo at Woodson Bend Resort
Beautiful condo at Woodson Bend! The kitchen is HUGE as well as the patio! We will definitely stay again!

On the Green 71-4 WB - Golf, Pool, Pickleball
Very cozy and very clean! We loved our stay!

Lovely 3-bedroom lake condo with golf and a pool
Enjoyed our stay. Nicely updated condo with plenty of room. Convenient to pool, playground and restaurant. Stools around the kitchen counter instead of table with chairs.

A Glimpse of the Lake (77-3) Golf Pool Pickleball
Great place peaceful âşď¸
Quick stats about holiday rentals with outdoor seating in Jamestown
Total rentals
30 properties
Nightly prices starting at
âš5,994 before taxes and fees
Total number of reviews
850 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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