Holiday rentals with a pool in Fitchburg

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

4.93 out of 5 average rating, 213 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

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.

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

4.98 out of 5 average rating, 167 reviews

*Holiday Getaway! Fireplace, Hot Tub, Fire Tables*

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

Cabin in The Galena Territory

4.95 out of 5 average rating, 167 reviews

Fall Fun! Hot tub-Fires in/outdoor-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 10 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 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.

4.94 out of 5 average rating, 168 reviews

Awesome Lodge in Galena Territory

Bring the whole family to our Galena home for fun, games, and making memories! Located 1.3 miles from the Owner's Club in The Galena Territory, enjoy many amenities and everything Galena has to offer! 15 mins to downtown! 3 bedrooms and 3 full bathrooms, the house is equipped with great Wi-Fi and 8 key cards to access Territory amenities! There is tons of space to spread out across 3 floors . Enjoy the game room, hot tub, three seasons room, deck, and outdoor space in this awesome home!

A cozy living area is featured with a warm fireplace and a mounted television above it. Two side tables are positioned beside the fireplace, enhancing comfort. Natural light enters through the windows adorned with wooden blinds, creating an inviting space for relaxation.

4.98 out of 5 average rating, 152 reviews

Last Fall Colors • Cozy King Bd • Fireplace • Pool

⭐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 and tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — enjoy boutique shopping, excellent dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool ⭐15 miles to Chestnut Mountain Skiing ⭐Steps from semi-private outdoor pool

A warm living area features a brick fireplace with a mounted television above it. Large skylights and windows allow natural light to fill the space. A coffee table stands at the center, adorned with decorative items, complemented by comfortable seating and a vibrant area rug.

4.96 out of 5 average rating, 109 reviews

Secluded Treehouse, w/great views, close to Hwy 20

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

Treehouse in The Galena Territory

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

4.98 out of 5 average rating, 184 reviews

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

A gravel fire pit area is positioned in the foreground, surrounded by a circular stone border. The spacious yard is framed by trees, providing a natural setting. In the background, a cozy wooden house with a deck is partially visible, blending harmoniously into the landscape.

4.95 out of 5 average rating, 255 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

A spacious living area features soft seating arranged around a circular glass coffee table. A large window allows natural light to fill the room, with a view of the outdoors visible. A stone fireplace and wall-mounted television enhance the cozy atmosphere.

4.94 out of 5 average rating, 174 reviews

The Beauty on Belden: Owners' Club access & more!

Our 3 bedroom, 3 bathroom retreat located in the Galena Territory is the perfect choice for your getaway with access to the Owners' Club. Each bedroom has its own private bathroom. The four seasons room is perfect for relaxing. The home has a spacious back deck for cookouts and entertaining. The house is a 3 minute drive from the Owners' Club and minutes away from 4 golf courses, Shenandoah Riding Center and Marina. 10 minutes to downtown Galena, 15 min to Chestnut Mountain.

4.96 out of 5 average rating, 137 reviews

A two-story house is set on a spacious lawn, framed by trees exhibiting autumn colors. The exterior features a welcoming porch with white railings. A paved driveway leads to a garage, and a privacy fence encloses the backyard, contributing to a tranquil environment.

Home in Spring Green

Hot Tub/$0 Cleaning Fee/Golf Course/The 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.

Holiday 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.

4.96 out of 5 average rating, 127 reviews

Fall Escape | Hot Tub, Fire Pit & Galena Views

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.

Popular amenities for Fitchburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 88 reviews

The Ho Hum East on Apple Canyon Lake

A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

5 out of 5 average rating, 76 reviews

Stunning 5 bdm home on The General in Galena Terr!

4.89 out of 5 average rating, 74 reviews

2 BR l 4 beds w/Game Room, Fire Pit & Star Gazing

5 out of 5 average rating, 12 reviews

A modern multi-level home is shown from the exterior, with a large deck extending from the second floor. A swimming pool is visible in the foreground, surrounded by a grassy area. The backdrop features a wooded landscape under a clear blue sky.

Home in Portage

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

A modern, two-story house is set against a lush green landscape, featuring dark exterior siding and a pitched roof. A welcoming entrance is framed by two white chairs on a front porch, with trees and a bright blue sky in the background.

5 out of 5 average rating, 12 reviews

Modern Home in Galena Territory

A charming two-story home is set among lush greenery, featuring a welcoming porch and a winding pathway leading to the entrance. Surrounding trees offer a sense of seclusion, enhancing the natural environment of the location.

4.92 out of 5 average rating, 170 reviews

DunPuttin Place

4.97 out of 5 average rating, 100 reviews

Home in Rockton

HD Jameson House at River’s Edge

A welcoming sign is positioned near a large tree, directing guests to a modern home. The house features a sloped roof and is partly surrounded by lush greenery. A winding driveway leads up to the residence, set against a backdrop of rolling hills.

4.98 out of 5 average rating, 45 reviews

Charming Galena Getaway

Apartment rentals with a pool

The exterior of a resort building is showcased, featuring a combination of brick and timber elements. Large windows and a main entrance are visible, framed by well-maintained landscaping and shaded by surrounding trees. The sky is bright, adding to the inviting appearance.

Wyndham Galena Resort |2BR/2BA King Bed Balc Suite

The exterior of the resort showcases a blend of stone and timber materials, complemented by spacious balconies. Large windows allow natural light to fill the interior. A wide lawn area is bordered by towering trees, creating a serene environment. The sky is bright with soft clouds.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

A lodge-like building with a combination of timber and stone features is situated along a tree-lined path. The structure has multiple balconies and large windows that invite natural light, framed by vibrant green trees on a clear day.

Wyndham Galena Resort |2BR/2BA King Bed Balc Suite

The resort's exterior showcases a blend of brick and timber architecture, framed by expansive green lawns and mature trees. A central entrance can be seen, leading to stylish accommodations with balconies visible on the upper level, under a clear blue sky.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

Superhost

A comfortable living area features a dark leather sofa adorned with decorative pillows. A light-colored coffee table with a woven basket sits centrally. Two lamps provide soft lighting, while a staircase is visible in the background, leading to the upper level.

5 out of 5 average rating, 3 reviews

Golfer's Valleywood Getaway

A charming lodge-style building features a mix of stone and timber exteriors. Large windows reflect natural light, while expansive balconies overlook a manicured lawn. A shaded area is created by a large tree, adding to the serene ambiance of the resort.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

The exterior of a rustic lodge features a combination of stone and timber accents under a clear blue sky. Tall trees provide shade in the foreground, while the building's expansive façade and multiple balconies are visible, inviting relaxation and natural scenery.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

The exterior of a lodge-style resort is depicted, featuring a mix of stone and timber elements. Large windows and balconies invite natural light, while an expansive green lawn and trees create a peaceful setting. A stone pathway leads towards the entrance.

4.88 out of 5 average rating, 8 reviews

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

Other holiday rentals with a pool

A spacious living area features a dark couch adorned with yellow pillows. A wooden coffee table sits in front, showcasing vases with dried flowers. A textured rug covers the floor, while large windows invite natural light, illuminating the handmade wall art above the couch.

4.84 out of 5 average rating, 51 reviews

Bluffwood Bungalow - Secluded, Forested Getaway!

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.

4.91 out of 5 average rating, 22 reviews

The Tree House

Cabin in The Galena Territory

A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.

4.99 out of 5 average rating, 87 reviews

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Cabin in The Galena Territory

A welcoming cabin exterior is framed by lush greenery, featuring a central entrance with a covered porch. The gentle slope of the pathway guides visitors toward the door. Large windows allow for natural light, while surrounding landscaping adds a touch of nature.

4.92 out of 5 average rating, 75 reviews

The MacRae Cabin

The exterior of the home features a mix of stone and siding complemented by multiple large windows. The structure is surrounded by well-maintained green grass and rolling hillside views, with a spacious deck area accessible from the main living spaces.

4.95 out of 5 average rating, 37 reviews

Galena Retreat-Cogan View!

Cottage in The Galena Territory

A spacious outdoor porch features log pillars and stone accents, offering seating with a wooden rocking chair and a small table. The view showcases the tranquil lake, surrounded by lush greenery and distant hills under a clear blue sky.

4.86 out of 5 average rating, 22 reviews

The Cottage on Lake Galena

A spacious living area is bathed in natural light from large windows, showcasing views of the surrounding woods. A comfortable sectional couch is positioned for relaxation, while a modern fireplace and mounted television enhance the casual ambiance. A telescope is available for stargazing.

4.95 out of 5 average rating, 64 reviews

Longwood Lodge

A cabin nestled among the trees features a wooden exterior with green siding. Steps lead to the entrance, bordered by lush foliage. The surrounding forest is dotted with young leaves and greenery, creating a serene natural setting.