Vacation 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, 215 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.

A spacious game room features a traditional billiard table set against a warm wood-paneled wall. Decorative elements include a dartboard and a wooden rack for cues. Natural light filters in from a nearby door, enhancing the inviting atmosphere of the space.

4.89 out of 5 average rating, 109 reviews

Tranquil Home Away From Home

This home has a relaxing atmosphere, surrounded by woods and wildlife. Though, still easily accessible in the Galena Territory. You'll be sure to have a relaxing and wonderful time, in it's superbly decorated interior. Featuring farmhouse and country styles all it's own. The rolling hills of the area are beautiful in every season and the Galena area has lots to offer it visitors, golf, historical buildings, antiquing, fishing and boating on Lake Galena, canoeing and biking along the Galena River

The exterior of a charming blue vacation rental showcases a welcoming front porch with seating. A stone pathway leads through landscaped areas with plants, approached by a warm sunset sky. The structure features multiple windows, allowing natural light to illuminate the inviting entryway.

4.97 out of 5 average rating, 108 reviews

Hot tub | 3BD|3BA en-suites | Resort Amenities

Leave your worries behind at our 3-bed, 3-bath vacation rental in The Galena Territory. Our updated home offers a fully equipped kitchen, screened-in porch for enjoying your morning coffee, a furnished deck with a grill, and access to amenities such as a fitness center and indoor/outdoor pools. Explore all Galena has to offer! Stroll historic Galena, visit Ulysses S. Grant's Home, hike the various trails in the territory, or race down to the banks of the Mississippi at Chestnut Mountain Resort!

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, 174 reviews

*Winter 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

A spacious living area features light wood flooring and neutral-colored walls. A large window provides natural light and views of the outdoor space. Comfortable seating includes two armchairs and a sofa, with a coffee table centered on a patterned rug. A brick fireplace adds an element of warmth.

4.85 out of 5 average rating, 104 reviews

Best Pool View 2 BR 2 BA Abbey Villa D

Pool view sunlight Villa. It's great for a girls weekend, golfing trip or a family reunion. The condo next door is also available. Located adjacent to the Abbey Resort, Avani Spa & Big Foot Golf. Our 2-bedroom, 2-bath Villa features an open floor plan and has the comforts of resort living, including a pool. The second floor, walk-up unit has an outdoor dining area with seating for six and and a deck overlooking the pool and grounds. Essentials included. No parties. New pool coming summer 2026!

Cabin in The Galena Territory

A cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.

4.98 out of 5 average rating, 153 reviews

*Hot tub-Fire-3 king beds-Game room*Winter fun!*

Relax, unwind, & explore at this winter retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and winter adventure!

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

4.9 out of 5 average rating, 142 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

Golfer? Inquire for(e) for details on our Golf Packages. Welcome to The Nest, a beautifully updated and dog-friendly home in The Galena Territory. This spacious home features 3 BR & 3 full bathrooms all on different levels, each with a Smart TV. Enjoy the large kitchen and dining room, multiple patios, & two cozy living rooms with fireplaces. Soak in the hot tub after a long day of adventures in Galena. The Nest has a max occupancy of 8 guests. Access to Owner's Club amenities included.

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, 192 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

Cabin in The Galena Territory

The exterior of the cabin features a welcoming wooden facade complemented by a front porch with a railing. A well-kept garden with various flowers rests by stone steps leading up to the entrance, surrounded by lush greenery and natural elements.

4.89 out of 5 average rating, 131 reviews

Serenity Cabins - A rustic, yet upscale cabin!

Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities while feeling the rustic atmosphere. You can fall asleep with the sounds of nature and the whispers of the winds. Go for quiet walks as you surround yourself by nature's natural beauty or unwind in front of the fireplace.

4.95 out of 5 average rating, 259 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, 179 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.

Popular amenities for Fitchburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.89 out of 5 average rating, 28 reviews

The Tree House

The exterior of the home is showcased, highlighting a multi-level structure surrounded by lush greenery. Large windows reflect warm indoor lighting, and a spacious deck is visible, featuring Adirondack chairs positioned near the lawn, offering ample space for relaxation and outdoor enjoyment.

4.96 out of 5 average rating, 98 reviews

Treehouse • Hot Tub + Firepit • Serene Retreat

5 out of 5 average rating, 12 reviews

Home in Portage

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

4.92 out of 5 average rating, 37 reviews

A charming two-story house with a front porch is surrounded by lush green grass and trees. The property includes an additional structure to the right, showcasing a well-maintained landscape that enhances the serene atmosphere of the setting.

Home in Albany

Sunset retreat oasis Pool hot tub river fishngame

A recreation room features a bright red pool table at the center, surrounded by comfortable seating. Large windows provide views of the outdoor landscape. A colorful map mural adorns the wall, complemented by modern decor and a vibrant ceiling design.

4.97 out of 5 average rating, 33 reviews

New/Fullyloaded/Golf sim/theater/Hot tub/Kingbeds

An outdoor seating area is arranged around a central fire pit on a spacious deck. Comfortable chairs with decorative pillows face the fire, surrounded by a plaid rug. Lush green hills are visible in the background, enhancing the tranquil outdoor setting.

4.98 out of 5 average rating, 66 reviews

Golden Meadows Escape: A Luxurious Country Retreat

4.86 out of 5 average rating, 29 reviews

A modern kitchen area is shown with white cabinetry and dark appliances. Two stools are positioned at the kitchen island, while a dining setting is visible. Light wood flooring complements the space, and a cozy seating area is framed by a neutral-toned couch and decorative rug.

Home in Cottage Grove

The Getaway Loft

4.97 out of 5 average rating, 100 reviews

Home in Rockton

HD Jameson House at River’s Edge

Condo rentals with a pool

5 out of 5 average rating, 3 reviews

Abbey Villa Corner 1st Fl Condo-BBQ,Walk to Pool

A bright and open living space is visible, showcasing a seamless transition from the kitchen to the dining area. Light wood floors run through the area, while large glass doors provide views of the outside greenery. Soft furnishings add a touch of comfort to the inviting atmosphere.

4.99 out of 5 average rating, 69 reviews

2 BD 2 BA Abbey Villa with Pool

The spacious living area features large glass sliding doors that open to a patio, allowing natural light to fill the space. A cozy sectional couch is complemented by a dark coffee table, with a rug adding warmth to the floor. A relaxed decor theme is evident throughout.

4.5 out of 5 average rating, 4 reviews

Fontana Abbey Villas Condo Steps to Pool and Beach

A serene marina scene is captured at sunrise, with boats docked in calm waters. Sunlight reflects off the lake, creating a glimmering effect. Lush green grass borders the scene, complemented by trees in the distance, enhancing the tranquil atmosphere.

5 out of 5 average rating, 21 reviews

Abbey Harborfront Villa on Lake Geneva

The kitchen features dark cabinetry against a brick wall, complemented by a large island with seating for six. Pendant lights hang above, illuminating the cooking area which includes modern appliances and tasteful decor. A dining table is positioned in the background, promoting an open-concept feel.

4.89 out of 5 average rating, 19 reviews

Abbey Villas Condo Steps to Pool Near Beach

4.33 out of 5 average rating, 15 reviews

Stylish Fontana Condo Near Lakes, Outdoor Pool, Ba

A lodge-style building is framed by large trees, with stone and timber elements defining its facade. Multiple levels of balconies provide access to outdoor spaces, while manicured greenery enhances the welcoming appearance of the entrance.

Condo in The Galena Territory

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

The modern kitchen features a spacious island with granite countertops, accompanied by several bar stools. Sleek cabinetry and stainless steel appliances create a functional cooking space. Large windows allow natural light to fill the area, with views of the surrounding environment visible outside.

4.31 out of 5 average rating, 13 reviews

Stunning Pool View Condo at Abbey Villa

Other vacation 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!

A spacious living area highlights a stone fireplace framed by large windows that offer views of the surrounding trees. Comfortable leather sofas and armchairs are arranged around a wooden coffee table, creating an inviting space for relaxation and conversation.

4.81 out of 5 average rating, 64 reviews

Our Lodge in the Big Woods

A cozy bedroom features a wooden bed frame with a patchwork quilt displaying nature-themed designs. Two decorative pillows rest on the bed. A wooden dresser displays decorative items, and the wall is adorned with subtle forest-themed decorations. Ample closet space is available with wooden sliding doors.

4.97 out of 5 average rating, 37 reviews

Deerview

A dining table set for two is positioned on a wooden deck, surrounded by green foliage. Two plates and glasses with garnishes rest on a glass tabletop, with a bottle of wine nearby. Chairs are arranged around the table, offering a cozy outdoor dining experience.

4.95 out of 5 average rating, 41 reviews

Tantalizing Game Room/Fab Screened Porch/Fireplace

A hot tub filled with bubbling water is situated in a serene outdoor setting, surrounded by lush trees. The warm light of the setting sun filters through the branches, creating a calming atmosphere for relaxation.

4.51 out of 5 average rating, 47 reviews

6BR Galena Territory Amenities | Private Hot Tub

Cabin in The Galena Territory

A spacious living area features a stone fireplace surrounded by large windows that provide natural light. Comfortable seating arrangements include leather couches and a wooden coffee table. A large television mounted on the wall displays a serene landscape. Soft lighting enhances the inviting ambiance.

4.96 out of 5 average rating, 51 reviews

Hot Tub and Firepit at Beautiful Fall Retreat

A spacious living room is illuminated by natural light from large windows, highlighting a cozy wood-burning fireplace. Comfortable seating is arranged around a central coffee table adorned with a vibrant floral arrangement. A Smart TV is mounted above the fireplace, enhancing the room's inviting ambiance.

5 out of 5 average rating, 14 reviews

Galena Retreat: 4 King Rooms, Hot Tub & Pool Table

The exterior of a modern cabin is framed by lush green foliage. The structure features a prominent a-frame design with large glass windows and a spacious balcony. The surrounding lawn is well-maintained, showcasing the home's integration into the natural landscape.