Holiday rentals with a pool in Fitchburg

4.54 out of 5 average rating, 41 reviews

A rustic cabin features a combination of log and stone materials with a sloped roof. A spacious front porch, supported by wooden pillars, overlooks a grassy area bordered by trees. The surrounding landscape is serene, providing a calm and inviting atmosphere.

Cabin in Elizabeth

Gleneagle Suite

Homestead Hideaway offers you a unique opportunity to rest & relax within a peaceful setting.Located just 15 Miles from Galena, Illinois, our cabins in the woods can be your home away from home while you enjoy Galena,Chestnut Mountain, hiking, wineries, and all the other amenities Jo Daviess County has to offer. The Gleneagle Suite is our weekend getaway suite. It is a studio style and below another rental.(like a duplex setting)full kitchen, living area, dining area, bathroom & a full size 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.

Home in Sun Prairie

New place to stay

Hot Tub - Private Pool - Game Room - 20 min DT

🔹Private fenced in backyard w/ heated pool w/ pool toys & HOT TUB 🔸Outdoor living w/ lounge seating on the deck, gas grill, outdoor dining & fire pit 🔹Sleeps families & groups - 2 King, 5 Queen 🔸Game room w/ pool table, smart tv, board games, & gas fireplace 🔹5 min to Sun Prairie restaurants & shopping 🔸Pets welcome 🔹Highchair & pack n’ play on site 🔸You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 20min

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, 89 reviews

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

Guest house in Beloit

Spacious Delightful 2 Bedroom Home

Entering the front door you'll feel right at home. Full Bathroom with walk-in shower and amenities. Living Rm and separate Reading/Work Den with 60" HD Roku TV. Complete Fully Functional kitchen. An additional Twin or Queen size air bed, set up with bedding, is available by request to sleep a total of six. Conveniently close 2 min. from Beloit Hospital, Grocery Store, Drug/Convenience Stores, restaurants, bike/hiking paths along the scenic Rock River, Beloit College and Downtown activities.

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

Take it easy at this unique and tranquil getaway. romantic dinners. tranquil evenings. pool and hot tub. big yard. Foosball . yard games. close to ice age trail and multiple parks dams and waterfalls. . neibors r cool. u should be too. available for tubing and kayaking thru snb or minihaha. sugar river raceway. New Gllarus brewery and Monroe shops. bonfires n cookouts. bands down the road on sat. parties available 4 rental of both houses. please enquire. extra or tenting available.

4.98 out of 5 average rating, 52 reviews

Cabin in Lodi

Modern Cabin with pool, hot tub and outdoor sauna

Forget your worries in this spacious and serene space. Secluded yet close to a big city (Maddison and Wisconsin Dells) and lots of entertainment! 20 min away from 2 ski resorts, an amazing winery and distillery, spas, restaurants, casino! 3 mile away from lake Wisconsin. Hiking trailers, 24 hour ferry service across the lake and more. This luxurious villa combines comfort and style, you won't want to leave it, but the area is full of enviting places to go to, so plan for a few extra days!

4.95 out of 5 average rating, 22 reviews

The exterior of the cabin features a modern design with a sloped roof, set in a lush green landscape. Tall grasses frame the building, and a deck with seating is visible, providing a peaceful spot to enjoy the surrounding nature.

Home in Dodgeville

Little Eden

A little Eden in the Town of Eden. This mod 1972 cabin is just four miles West of Dodgeville, nestled in a secluded glen with private pool, staggering views, 60 acres of hiking, hunting, or trout fishing, two decks, and access to all the Driftless Region is known for: hiking, biking, antiquing, thrifting, fine and regional dining, American Players Theater, Taliesen, House on the Rock, and Potosi Brewing Company. This place is perfect for two families or one big one, or a group of friends.

4.97 out of 5 average rating, 100 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.

4.96 out of 5 average rating, 138 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.

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

The perfect place to relax, play and explore. Three levels of luxury and drenched with natural light. Wolf/Sub Zero/Miele kitchen. Kohler fixtures and spacious tiled showers for self pampering. Restoration Hardware furniture & two 77” TV's 5 Deck Areas: sip coffee, sun bathe, read, yoga sessions * Pickleball * Clearlight Infrared 4 person Sauna * 9 Person Hot Tub * In-ground Pool 48' x 24' with Sun Deck * 13 acres * Nearby ski, golf, Wis. Dells, Madison

4.97 out of 5 average rating, 29 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.

Flat in Middleton

Private yet close to everything!

Our 900 sqft basement apartment features a master bedroom, connecting kitchenette/sitting room, and bathroom. We are a 20-minute drive to the UW campus, Capitol Square, and Dane County Airport—minutes from Middleton Pheasant Branch Conservancy for hiking and biking. Madison and Middleton consistently win "Best Places to Live" awards for quality of life. As past Superhosts, we are excited to start hosting again after COVID!

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

A stone fire pit is depicted in the foreground, with flames brightly rising as the sun sets in the background. The calm water reflects the evening light, and several leafless trees are visible, adding a serene ambiance to the scene.

5 out of 5 average rating, 4 reviews

Lakefront cabin in the woods.

4.88 out of 5 average rating, 17 reviews

A serene backyard scene features a clear blue swimming pool surrounded by a spacious patio. Comfortable seating arrangements, including lounge chairs and a patio table with chairs, are positioned nearby. A red patio umbrella provides shade, and lush greenery frames the area, enhancing the outdoor setting.

Home in Fitchburg

Country Living/Downtown Access

A spacious outdoor area features a sparkling swimming pool surrounded by stamped concrete. A covered seating area offers comfortable chairs. Lush greenery frames the space, and vibrant murals decorate the adjacent wall, creating a lively and inviting atmosphere. Colorful pool floats rest on the water.

Home in Edgerton

4.74 out of 5 average rating, 39 reviews

Boat Dock & Backyard: 'Rock River Retreat'

A two-story home is depicted, surrounded by a well-manicured lawn and various shrubs. The inviting entrance features a porch with white railings. A spacious driveway leads to a garage, and trees dot the landscape, offering a sense of openness in the rural setting.

Home in Poynette

4.81 out of 5 average rating, 47 reviews

Your Home Away From Home!

5 out of 5 average rating, 86 reviews

An outdoor balcony features a large table surrounded by six chairs, with a bright red umbrella providing shade. Green Adirondack chairs are positioned nearby, overlooking the grassy lawn that leads to the waterfront.

Home in Janesville

Family Home w/ Deck, Yard, Dock on Rock River

An expansive outdoor deck is revealed, featuring a canopy-covered dining area alongside several lounge chairs. Umbrellas provide shade over seating arrangements, surrounded by lush trees. A glimpse of a pool is visible in the background, enhancing the inviting outdoor space.

Home in Madison

4.89 out of 5 average rating, 288 reviews

Luxurious BBQ and Pool House

Home in Apple Canyon Lake

A spacious living area is highlighted by a wooden ceiling and large windows. A dining table with intricate carvings sits nearby, complemented by comfortable seating arranged for relaxation. Soft lighting from a chandelier adds to the inviting ambiance of the space.

4.31 out of 5 average rating, 13 reviews

Log Home near amenities

A cozy living area showcases a large wooden coffee table centered on a geometric-patterned rug. A plush armchair and a soft sofa are positioned nearby, while a decorative vase with greenery and modern accents adds a touch of style. Light enters through large windows, enhancing the space.

Home in Verona

Luxurious Bright Golfing Oasis!

Other holiday rentals with a pool

A light blue cabin is nestled among the greenery, surrounded by trees that provide a natural setting. A small wooden deck is visible at the front, offering outdoor access. Large windows allow for ample daylight, creating a bright and welcoming atmosphere.

Sunset Hollow PM13

A well-maintained park model home is showcased against a backdrop of lush green grass and tall trees. A wooden deck with a railing surrounds the entrance, and a barbecue grill is positioned nearby, offering options for outdoor dining.

5 out of 5 average rating, 3 reviews

Whispering Pines PM10

A quaint cabin features a weathered wood exterior and a welcoming porch with railing. Surrounded by lush green pine trees, the setting offers a natural and peaceful atmosphere. A picnic table and grill are positioned nearby for outdoor activities.

4.67 out of 5 average rating, 12 reviews

Tranquil Trails Cabin 87

The rustic cabin, constructed from wood, is set within a natural garden, surrounded by greenery. A covered porch with a railing is visible at the entrance, leading to a white door. Picnic tables can be seen nearby on the well-maintained grounds.

Summit View Cabin 94DL

A wooden cabin features a covered porch with two chairs and a small table, surrounded by natural greenery. The front door is flanked by two windows. A row of lounge chairs extends alongside the tranquil lake, inviting relaxation and enjoyment of the serene surroundings.

5 out of 5 average rating, 3 reviews

Serenity Shores Cabin 63BC

A charming wooden cabin is nestled among trees, showcasing a simple front porch with two chairs. A rustic picnic table sits nearby on a gravel surface, surrounded by lush greenery, enhancing the serene and natural setting.

Cozy Cabin 80

A quaint red cottage is viewed from a distance, surrounded by lush greenery. A picnic table stands to one side, while a fire pit is positioned in front. The path leading to the entrance is lined with grass and dirt, creating a welcoming approach.

Charming Nook Cabin 97

A small, charming cabin with a wooden exterior stands surrounded by greenery. The front porch features a white door and steps leading up to it. A fire pit is located on the grassy area nearby, adding to the outdoor experience.