Vacation rentals with a pool in Appalachian Mountains

Cataloochee Sky *private spring fed pool & hot tub

This VERY RUSTIC, contemporary home designed by Norwegian architect, Bernardo Rostad, is situated at the foot of the Great Smoky Mountains National Park & adjoins the renowned Cataloochee Ranch. Enjoy spectacular sunrises from the east facing windows perched high above the clouds at 4,700 ft elevation w/ 360 degree views of the Smoky Mountains, located on 25 PRIVATE acres. *See "THE SPACE" description below & confirm that you have read prior to booking request. Reply: I have read "THE SPACE".

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Historic Farmhouse w/ Pool & Wood-fired Hot Tub

This authentic 1700s farmhouse has 3 bedrooms with a seasonal pool and a wood-fired hot tub on a bucolic 13-acre property. Minutes away from Van Sant Airport, Lake Nockamixon, and the Delaware Canal, this charmingly rustic home has modern amenities, central AC, barn door kitchen cabinets, and a large stone fireplace equipped with a wood burning stove. The property is perfect for small groups of friends and family who enjoy peaceful country life. The house sleeps 5 people and is dog-friendly.

Luxurious Peaceful Chalet

New 7 SEAT HOT TUB! In the heart of Pocono Mountains a newly renovated, modern, spacious & family-friendly chalet in an amenity filled community Private 3000sqft 4bed3bath home located on 1.5acres backing up to a nature preserve Enjoy the sauna, hot tub, game room, fireplace, fire pit We are in a community with 5lakes, 3beaches, fishing lake, 2pools, playgrounds, tennis & basketball courts Minutes from bird watching, hiking, wineries, skiing, indoor water parks, golfing & casinos

Historic Rousby Hall, Waterfront, Pool, Beach

*Heated pool open to Nov 2* Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool (May–October) with amazing river views. The estate also hosts weddings and events for up to 100 guests (additional event fee applies).

Mid-century A-frame nestled amongst the trees

This little A-frame is a mid century dream nestled among the trees in the Pocono Mountains of Northeastern Pennsylvania and is within a few minutes walk to the lake. Beautifully and loving curated, filled with mid- century furniture, lots of art, books and records. A highlight of the cabin is the upstairs bathroom, featured in Condé Nast, Houzz and West Elm, it's a Pinterest dream come true. Come take a soak in our beautiful soaker tub among the trees. 2 hours from NYC.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Countryside Suite

Take a break and unwind at this peaceful oasis. This beautiful, cozy countryside suite is located in an area where there is a lot to do. If you like the outdoors, shopping, wineries distilleries, breweries or just plain relaxing in the country, this is the place for you. We are a short driving distance to all local restaurants, hiking/biking trails, kayaking, and shops. Access to the pool and a private patio are included in the price of the rental.