Vacation rentals with a pool in Winchester

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Cabin in Bryant

4.95 out of 5 average rating, 141 reviews

Chatt. Tn 21 miles! Pool*AweSOME*HotTub*FirePit!!!

SUNDAY check in ALLOWED except 4th Sunday of each month POP & GRANNY'S CABIN is located inside Paradise Pointe which is gated & on a mountain, tristate corner of AL/TN/GA. HIKING TRAIL to tristate corner. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck-19 rentals has access to pool house. WIFI, hot tub, fireplace, grill & fire pit! Main floor-BDR 1/king, Upstairs-BDR 2/king, BDR 3/family room has true queen bed & sectional & BDR 4/king Other rentals! paradisepointe.holidayfuture

Sep. 23 – 30

$409 CAD per night

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 24 reviews

Cozy Lake Cottage W/ Kayaks, SUPs, Pool & Firepit

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This cozy cottage is in a beautiful gated community and has lake views from the front porch. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for kayaks and paddleboards that we include for you! This beautiful home also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

Sep. 5 – 12

$361 CAD per night

Guest favourite

Condo in Chattanooga

4.9 out of 5 average rating, 211 reviews

210 Luxury _ Condo _ Riverfront & Downtown

A classy, chic one bedroom and bath in adventurous downtown Chattanooga. Great location and walking distance to so much that Chattanooga has to offer. Feel at home away from home with everything you need for an enjoyable stay. Decorated with up-scale furnishing and posh linens as well as a fully stocked kitchen. The amenities offer a great community room for guest to enjoy. Stay on track with access to the fitness center. Cool off in your seasonal outdoor pool or relax by the fire pit.

Nov. 8 – 15

$186 CAD per night

Guest favourite

Condo in Chattanooga

4.94 out of 5 average rating, 422 reviews

Luxury Downtown Oasis | Fully Disinfected

Beautiful Downtown Riverwalk Oasis THE CONDO This condo is a new downtown oasis!!! Designed and furnished to give our guests a modern and luxurious experience while also capturing the comforting feeling you can only get from being in a family home. Everything you could want downtown Chattanooga is at your finger tips. The Aquarium, The River Walk, Restaurants, Bars, Coolidge Park and much much more are within minutes reach. You will also have access to our Pool, Gym and Clubhouse!!!

Jun. 30 – Jul. 7

$378 CAD per night

Guest favourite

Condo in Chattanooga

4.9 out of 5 average rating, 314 reviews

407★Walk2Aquarium★2QueenBD★Topfloor

This is a NEW DOWNTOWN condo with top floor Balcony. It has a completed modern kitchen and a newly finished bath, equipped with luxurious and classy furniture and fine bedding, and all the essentials you will ever imagine. One free parking space is also provided for your stay. This condo is located in the heart of Chattanooga Downtown, close to popular attractions like the Aquarium, Museums and Restaurants, etc. Easy access to I-24,27 and 75. Ideal for family reunions and sightseeing.

Jul. 24 – 31

$259 CAD per night

Guest favourite

Vacation home in Winchester

4.93 out of 5 average rating, 14 reviews

Lakeside Laurel | Community Pool & Lake Access

Welcome to Lakeside Laurel. Come relax in the idyllic gated community of Barefoot Bay. • Community lake access steps away from home • Fantastic community pool & clubhouse for the hot summer days • Secluded backyard area complete with Traeger pellet grill & YETI cooler + cornhole & fire pit • Two inflatable stand-up paddleboards provided • Lake views from the master bedroom balcony • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

Aug. 27 – Sep. 3

$354 CAD per night

Guest favourite

Barn in Unionville

4.97 out of 5 average rating, 196 reviews

Whiskey River Retreat-The Barn with minis

Named Airbnb magazine top 5 must-see destination.Tranquil haven on a secluded 100 acre farm 50 m to Nashville & legendary Uncle Nearest/Jack Daniels. Experience rustic charm, modern amenities, relax in the stock tank pool, stroll unique rock landscape, meet adorable miniature horses & donkeys, and unwind on the private patio & build a fire under starlit skies. Enjoy Nash Creamery, yoga/massage. "The Humble Baron's Longest bar in the world," & Arrington Vineyards, & kayaking nearby.

Oct. 7 – 14

$306 CAD per night

Guest favourite

Condo in Chattanooga

4.95 out of 5 average rating, 101 reviews

209 LUXURY DOWNTOWN 2BR / 2BA CONDO, Sleeps 6!

This luxury, newly constructed, professionally decorated condo is exactly where you want to be in Chattanooga-- within walking distance (< 1 mile) of the TN Aquarium, Ross's Landing (home to Ironman transition point, Riverbend Music Festival, etc), many restaurant-bars (including Parkway Pourhouse and Scottie's), and The Riverwalk, a 16 mile paved riverside path. Rock City, Ruby Falls are a 15 min drive away, and the UT Chattanooga is a 5 min drive. Access to pool and gym included.

Aug. 16 – 23

$345 CAD per night

Guest favourite

Condo in Chattanooga

4.95 out of 5 average rating, 118 reviews

402~New Riverfront Mid-Century Luxury Condo

Enjoy a New Mid-Century Modern Condo located in a prime location in Chattanooga within walking/biking distance of Ironman/Outdoor events, Aquarium, Southern Belle Riverboat, several restaurants and bars and It also is located a few steps away from Chattanooga's Riverwalk where you can bike, run, walk for 20 plus miles. It is a 5-15 minute car drive to most attractions that Chattanooga has to offer plus many restaurants and bars.stylish experience at this centrally-located place.

May 8 – 15

$223 CAD per night

Guest favourite

Condo in Chattanooga

4.95 out of 5 average rating, 133 reviews

Chattanooga Escape! Riverwalk, Aquarium & More

Enjoy our modern, well-equipped 2 bedroom, 2 bathroom condo with easy access to everything downtown Chattanooga has to offer! Just across the street from the Tennessee Riverwalk. Walk to Southern Belle Riverboat (12 min), Ironman staging (11 min), Playground (13 min), Aquarium & IMAX (19 min< 1 mile) and nearby: Creative Discovery Children's Museum, Restaurants, more. There are two restaurants across the street (Parkway Pourhouse and Scottie's on the River).

Jul. 17 – 24

$329 CAD per night

Guest favourite

Condo in Chattanooga

4.96 out of 5 average rating, 396 reviews

Stylish & Family-Friendly Downtown Condo with Pool

Retreat from your Chattanooga adventures to our downtown condo with comfortable furnishings, homey touches, and a corner for the kids with books and toys. Order in and watch Netflix on the couch or cook a family meal in the fully-equipped kitchen (kids' dinnerware included). Perfect for a family, two couples, or small group of friends, the condo has a shared gym, pool, & fire pit. This is the perfect base camp to check out all that Chattanooga has to offer!

Jul. 23 – 30

$254 CAD per night

Superhost

Townhouse in Chattanooga

4.83 out of 5 average rating, 121 reviews

Casa Vista | Downtown - Pool - Riverwalk

Welcome to Casa Vista. Our cozy, modern, townhome is strategically located at the base of Lookout Mountain and between the historic district of Saint Elmo and the vibrant food scene of Southside. Most of Chattanooga's main attractions are reachable in 5-10min. You can also walk to the trailhead of the 20+ mile Riverwalk. Ruby Falls and Rock City are just up the mountain from us. Traveling by EV? We’ve got charging stations right around the corner!

Jan. 6 – 13

$348 CAD per night