Vacation rentals with a pool in Fitchburg

Townhouse in The Galena Territory

A welcoming living area features a vaulted ceiling and large windows that provide views of the outdoors. A brick fireplace adds warmth, while comfortable seating is arranged around a coffee table. Soft lighting enhances the cozy atmosphere, complemented by decorative plants and artwork.

4.91 out of 5 average rating, 191 reviews

The Airy Aerie: Owners' Club access, golf nearby!

Welcome to the Airy Aerie: an avian themed townhome in the heart of the Galena Territory. Our space has been carefully curated to reflect the diversity of birds you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring granite countertops and stainless steel appliances. There is a loft space upstairs where a rollout twin bed can be set up. Our home can accommodate a maximum of 6 overnight guests (assuming 1 person on the twin rollout bed).

Guest suite in Spring Green

A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.

4.91 out of 5 average rating, 172 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

4.98 out of 5 average rating, 166 reviews

Wooded Villa with Resort Access, Fireplace, K Bed

⭐King bed with plush bedding in a peaceful, private setting ⭐Wood-burning fireplace — perfect for cozy evenings together ⭐2-minute drive to the North Golf Course, driving range, & Stonedrift Spa ⭐Wooded nature views & tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — excellent shopping, dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool & fitness center ⭐15 miles to Chestnut Mountain Skiing ⭐2 Full bathrooms & newer full size sofa bed

Cabin in The Galena Territory

The inviting main living area features a high wooden ceiling with exposed beams, a stone fireplace at the center, and ample seating options. Natural light floods in from large windows, illuminating cozy furnishings and warm earth tones throughout the space.

4.95 out of 5 average rating, 185 reviews

Family Winter Fun! Hot tub-Fireplace-Game room!

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 8 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

The living area showcases a spacious layout with a leather pullout couch and armchair, complemented by a modern coffee table. A smart TV is mounted on one wall, while an electric fireplace adds warmth. The kitchen features a bar with three stools, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 192 reviews

The Wanderlust at the Sunset Cove

Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

Townhouse in The Galena Territory

The living area features a comfortable sofa and a rustic coffee table atop a circular rug. A stone fireplace serves as a focal point, complemented by a vibrant artwork of a rooster above it. Natural light floods in through large windows, providing views of the outdoor patio.

4.98 out of 5 average rating, 131 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

Are you searching for a serene and idyllic countryside escape in a winter wonderland? Look no further. Our elegantly appointed farmhouse-inspired townhome is located in the picturesque Galena Territory, boasting an array of amenities such as indoor/outdoor swimming pools, a fitness center, game room, tennis courts, 20+ miles of hiking trails, a private lake and more. Surrounded by verdant hills, the home offers a peaceful retreat while being only 20 min from Chestnut Mountain Ski Resort.

4.97 out of 5 average rating, 101 reviews

Home in Rockton

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

4.97 out of 5 average rating, 151 reviews

A hot tub sits on a patio, surrounded by a well-maintained yard. Colorful fall foliage is visible in the background, with vibrant red and yellow leaves contrasting against a white privacy fence. Steam rises gently from the water, suggesting a warm and inviting experience.

Home in Spring Green

Cozy Home/Large Backyard/Privacy FenceThe Hemlock

Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

Cabin in The Galena Territory

A private hot tub is showcased on a covered patio, illuminated by soft string lights. A plush rug lies beneath, enhancing the cozy ambiance. Surrounding seating offers a relaxing atmosphere for enjoyable evenings under the stars.

5 out of 5 average rating, 185 reviews

Hot tub,Fireplace,Pool/Marina Access,Games, Space!

3br/3bth home - hot tub - Relax by indoor fireplace - 2 acres for privacy, especially in the back of the home with woods. - Outdoor firepit with wood provided - Year round community indoor pool and seasonal outdoor pool 🏊‍♂️🏊‍♀️👙🤿 - Great for kids or kids at heart- home has popcorn machine 🍿 - Axe throwing game - snow cone maker 🍧 - cotton candy maker - air hockey/ping pong table - hammock - Ms. Pac Man Arcade game - Large Connect 4 game - sleds - gym access

Vacation home in The Galena Territory

A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.

4.97 out of 5 average rating, 144 reviews

Hot Tub & Fire Pit | Galena Spring Escape

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.91 out of 5 average rating, 112 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone!

A welcoming living area is highlighted by a comfortable seating arrangement, featuring a leather sofa and accent chairs. Natural light pours in through the windows, illuminating the wood flooring and a stone fireplace. A large SMART TV is mounted on the wall, adding modern convenience.

4.97 out of 5 average rating, 499 reviews

COZY, Pickleball, Fireplace, Devils Lake

NO RESORT FEES, WATERFRONT Relax on the porch and watch the boats glide by, soaking in the serene lake views. Whether you're looking for relaxation or recreation, our condo offers the best of both worlds. Book your stay today and experience the ultimate lakeside escape! Resort-Style Amenities • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

Popular amenities for Fitchburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior view showcases a spacious two-story home with a screened porch and a large backyard. Seating is arranged around a fire pit, surrounded by green lawn. The property is complemented by trees and stone landscaping, with ample windows reflecting natural light.

4.97 out of 5 average rating, 155 reviews

Hot tub/Game Room/Fire Pit/Across street from Pool

A charming gray house is set against a backdrop of colorful autumn foliage. The front porch features a red door, framed by shrubs and well-maintained landscaping. A clear blue sky provides a bright contrast to the warm tones of the trees.

4.96 out of 5 average rating, 307 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

4.96 out of 5 average rating, 46 reviews

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

Cute and cozy 2 bedroom house perfectly located!

4.91 out of 5 average rating, 113 reviews

A cozy seating area features a blue sectional sofa complemented by two bedside tables with lamps. A vibrant green wall adorned with faux plants adds a natural element. A neon sign stating 'Wisconsin Dells' is prominently displayed above the sofa.

Home in Wisconsin Dells

Family-Friendly Dells Stay | Sleeps 8 + Jacuzzi

The exterior of the tree house is softly illuminated at night, showcasing large windows that reveal the warmth inside. A red-lit sauna entrance is visible on the side, while a cozy fire pit is situated nearby, inviting relaxation in the serene outdoor setting.

4.87 out of 5 average rating, 31 reviews

The Tree House

4.89 out of 5 average rating, 228 reviews

A warm and inviting living area features wood paneling and exposed beams. A spacious sofa, adorned with patterned throws, faces a large flat-screen TV. Natural light filters through sliding glass doors that lead to an outdoor space. A rustic stone fireplace adds a cozy touch.

Home in Wisconsin Dells

Spacious Pine Cabin at Island Pointe

The exterior of a spacious home is displayed, featuring a wraparound deck and large windows that allow ample natural light. Outdoor seating options, including blue chairs and a stone fire pit, are positioned on a grassy area surrounded by mature trees.

4.95 out of 5 average rating, 184 reviews

Awesome Lodge in Galena Territory

An outdoor deck features a spacious hot tub surrounded by a wooden railing. Nearby, two wooden benches and a table provide additional seating. Sunlight filters through the surrounding greenery, casting a natural warmth on the deck.

4.96 out of 5 average rating, 104 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

Condo rentals with a pool

A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.

4.9 out of 5 average rating, 116 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

The image displays a scenic view of a riverfront condo complex with balconies overlooking the water. A red boat is docked nearby, reflecting blue skies and clouds. Below, a cozy interior is showcased with a queen bed, a television, and a seating area featuring a fireplace and large windows for natural light.

4.92 out of 5 average rating, 289 reviews

1BR UpperDells Riverfront: Jacuzzi, Pool & Hot Tub

An indoor pool area is featured with large windows allowing for ample natural light. Two separate outdoor seating areas overlook the water, with patio chairs positioned along the poolside and balcony. A comfortable living room setup includes a sofa, coffee table, and window view of the surroundings.

4.83 out of 5 average rating, 254 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

A unique A-frame exterior features a mix of black wooden siding and natural brown shingles. A small patio area is visible with a round table and four black chairs, surrounded by well-kept shrubs and landscaped gravel.

4.9 out of 5 average rating, 111 reviews

Dells Retreat-A Romantic Haven-Jacuzzi,Pool&HotTub

The spacious living room features two comfortable sofas and a central coffee table. Soft lighting is provided by a side table lamp. Large windows offer natural light and views, complemented by warm, earthy wall colors and a patterned area rug beneath the furniture.

4.79 out of 5 average rating, 159 reviews

Beautiful Condo at Chula Vista!

4.96 out of 5 average rating, 167 reviews

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

Condo in Lake Geneva

LakeView-SummerPool-FamilyFriendly-CloseToTown

4.88 out of 5 average rating, 120 reviews

A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.

Condo in Lake Geneva

Lake Geneva relaxation!

A modern kitchen features wooden cabinetry, stainless steel appliances, and a spacious countertop with an island on wheels. The backsplash is adorned with a mosaic pattern, and ample lighting is provided by stylish overhead fixtures, enhancing functionality.

4.98 out of 5 average rating, 176 reviews

The Williamson's Waterfront Condo - Pickleball

Other vacation rentals with a pool

4.97 out of 5 average rating, 33 reviews

A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable chair sits beside a small side table. Soft lighting is provided by lamps on either side of the bed, and a window allows natural light to fill the room.

Apartment in Middleton

Private yet close to everything!

Home in Apple Canyon Lake

The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.

4.93 out of 5 average rating, 94 reviews

The Ho Hum East on Apple Canyon Lake

5 out of 5 average rating, 3 reviews

The image showcases a vibrant waterpark area at the resort, featuring colorful water slides and a large outdoor pool filled with sun loungers. The backdrop includes a multi-story building with an inviting design, set against a partly cloudy sky.

Condo in Sauk County

Wyn Glacier Canyon, 2 BR, 8 FREE WaterPark Passes!

Cottage in Wisconsin Dells

An indoor pool area is visible, featuring a variety of colorful water play structures, including a frog-shaped slide and small boats. Natural light is allowed in through large windows, illuminating the smooth surface of the water and creating an inviting space for families.

4.89 out of 5 average rating, 9 reviews

Ski @ Christmas Mountain Village - 2BR Cottage I

5 out of 5 average rating, 47 reviews

The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.

Condo in Lake Geneva

Chic Condo in Lake Geneva.

4.85 out of 5 average rating, 40 reviews

A cozy living room features two sofas, a lounge chair, and a stone-surrounded gas fireplace. Natural light filters in through a nearby window, creating a warm ambiance. Open shelving displays decorative items, and the kitchen area is visible in the background with modern appliances.

Villa in Wisconsin Dells

Ground level Poolside Villa on Lake Delton

4.98 out of 5 average rating, 55 reviews

Cabin in Lodi

Modern Cabin with pool, hot tub and outdoor sauna