
Vacation rentals with outdoor seating in Jamestown
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Top-rated accommodations with outdoor seating in Jamestown
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Jamestown outdoor seating rentals
House rentals with outdoor seating

Luxury Lake Home! Dock Holidays Lake View Inn
The house was perfect for our family reunion, and Teresea and Tim are incredibly kind and helpful hosts. The kitchen was well equipped with everything we needed to fix all our meals, the living area has comfortable furniture for a crowd to hang out together, and it was great to have so many main floor bedrooms with their own bathroom. We loved sitting out on the deck, and the view of the lake was even better than I'd expected from the photos. We highly recommend it and hope to return again next year ourselves!

2 Bedroom - 1.5 Bath Waterfront Townhouse
Great location, central to everything and easy to get in/out of. Would definitely stay here again

Beautiful Lakehouse near Grider Hill Dock
Had 10 guests, had plenty of room. Very large parking lot was perfect for trucks and boats. 15-20 minutes from Halcomb's Landing and the dam at Lake Cumberland. Looking forward to staying here again!

"Lake it Easy" at Conley Bottom & Lake Cumberland
Great house! No complaints at all! Have stayed 2 times this year and highly recommend it! Location is awesome if you want to be near Conley Bottom! It is walking distance!

Maple Bourbon House Downtown- Boat slip by request
I'm from Somerset and our family came into town for Thanksgiving! Our family has grown so big we can't all stay at mom's anymore. This place was PERFECT! The location was close to downtown and only a mile from our mom's. It was large so no one felt cramped. We had 4 children under 3 and they provided a crib and highchair...which we did use. We loved how it is an older home, but updated kitchen and baths. It did remind me so much of a house we lived in for several years on South Central Ave. We felt right at home from the minute we walked in. The bedrooms are large with plenty of room to stretch out...so much better than staying in a hotel. I honestly felt I could live in this house long term. We all thoroughly enjoyed our stay and have NO complaints. The owner has thought of everything that you would need for a very comfortable stay. I would stay here again!

Alle’s place near downtown
This was the second time we have stayed at this house in the past 5 months. It is always a nice, clean place to stay. It is convenient to all areas of Somerset. Lisa is always so accommodating when we stay. We highly recommend this property!

Beautiful Large Lake Cumberland House
Loved staying at Joe’s place. Our family stayed here over Christmas because it was our first Christmas after losing my father. They even provided a Christmas tree for us. I’m so thankful for a nice place to spend time with my family over the holidays!

The Bourbon House Newly Refreshed Family Friendly
Tammy was a great host. Very responsive to our needs. The home was clean and the description was accurate.
Apartment rentals with outdoor seating

Lake Escapes on the Square
This was my second time staying here. Such a great place in town. I hope I’m able to stay here every time I’m in Jamestown. Great host who’s super nice, helpful & quick to respond.

New near Jamestown Dock - B
We loved the privacy right in the middle of downtown Jamestown. The home was clean and provided everything we needed for a comfortable week long stay. We’ve already recommended to all of our family who also stay in the area. Heather was a great host with quick responses to our messages. We greatly appreciate a home that we can bring our two little dogs with us. Thanks for a great experience!

Resort Clubhouse
At check in there was a hiccup with the pool that couldn't be avoided that it was not operable but we got later in that night anyway but by the next day it was working and the kids were excited. The pool was very warm which was awesome and right outside the door. The place was very big and accommodated for everyone. To be honest this was probably the best airbnb we have ever stayed at

Woodson Bend Resort getaway on Lake Cumberland.
Christopher’s 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 Christopher’s place in Woodson Bend!

New near Jamestown Dock - A
Will be back. Great place

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 isn’t 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.
Condo 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. Debbie’s place is clean, well stocked and as it is shown in the pictures and description.

Amen Corner at Woodson (46-3) Golf Pool Pickleball
We have been going to Woodson Bend since I was a kid. We finally outgrew my parents place and needed a place of our own. We had a great stay at this Condo. We have 4 kids and the bunk beds were great, the condo was clean, and they had very detailed instructions.

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.
Quick stats about vacation rentals with outdoor seating in Jamestown
Total rentals
30 properties
Nightly prices starting at
$97 CAD 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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