Vacation rentals in West Point

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Top-rated vacation rentals in West Point

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Guest favorite

Guest suite in Spring Green

4.9 out of 5 average rating, 112 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.

Oct 7 – 14

G$26,775 GYD per night

Guest favorite

Cottage in Poynette

4.97 out of 5 average rating, 190 reviews

Lake Wiscosnin Cozy Cottage

Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi

Sep 15 – 22

G$28,195 GYD per night

Guest favorite

Guesthouse in Wisconsin Dells

4.83 out of 5 average rating, 247 reviews

Waterfront Cottage with beautiful views

This waterfront cottage has beautiful views of the Wisconsin River. My husband and I have lived here for more than 20 years. We love this area - there is nothing like a cool, crisp Midwest morning overlooking the Wisconsin River. Or enjoying a great glass of wine (or Wisconsin beer) while watching a spectacular summer sunset from the deck. Expect peace and tranquility as we are far enough from Downtown Dells to avoid the crowds and noise. We look forward to hosting you and your loved ones.

Oct 3 – 10

G$16,503 GYD per night

Guest favorite

Cottage in Arena

4.91 out of 5 average rating, 263 reviews

Sugarland Cottage

The Sugarland cottage is designed to accommodate up to 8 guests. It has a full kitchen, bathroom with shower, two bedrooms, one with a queen bed and the other with a double and 2 twin beds. Downstairs is a pull out queen sized Murphy bed. Situated in a major southern Wisconsin tourism area, Sugarland cottage is close to the Wisconsin River and only 30 minutes from Madison and 10 minutes from Spring Green home of Frank Lloyd Wright’s Taliesin, American Player’s Theater, and House on the Rock.

Aug 28 – Sep 4

G$27,044 GYD per night

Guest favorite

Guest suite in Middleton

5.0 out of 5 average rating, 115 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with two skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house but has its own outdoor entrance and is soundproofed for privacy. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Sep 25 – Oct 2

G$18,016 GYD per night

Guest favorite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 247 reviews

Entire Countryside Garden Suite, Peaceful Retreat

Welcome to our home! We have upgraded our Garden Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Jan 6 – 13

G$18,140 GYD per night

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 245 reviews

Historic guesthouse near downtown, hospital and UW

Featured on the National Register of Historic Places, this unique 1916 “granny cottage" stands behind our home in the gorgeous Village of Shorewood Hills. Centrally located, we are just a few walkable blocks from UW Hospital and Picnic Point, and walking/biking distance from UW, the Capitol, Hilldale Shopping Mall, Whole Foods and plenty of restaurants. Because we are in a quiet neighborhood, we have a 3 guest maximum. This is a place to retreat and relax and enjoy the best of Madison.

Sep 8 – 15

G$29,531 GYD per night

Guest favorite

Guesthouse in Poynette

4.93 out of 5 average rating, 222 reviews

Simple Cabin*Lake View rustic cabin in rural WI

The Simple Cabin on Lake Wisconsin is a simple and clean space. It would be ideal for an individual or couple who are enjoying the beautiful outdoors by day, and would like a bed by night. It is 350 sq ft for the entire cabin consisting of bedroom, small full bathroom, and living area. You will enjoy 180 degrees of across-the-water views. It's a great hub for hiking with the following all within 15 - 35 minutes: Devil's Lake, Parfrey's Glen, Gibralter Rock (ice age tr) & Mirror Lake.

Sep 24 – Oct 1

G$30,334 GYD per night

Guest favorite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

Oct 11 – 18

G$22,358 GYD per night

Guest favorite

Cabin in Baraboo

4.98 out of 5 average rating, 266 reviews

Private Baraboo Bluffs Cabin with Peacocks!!

This is a beautiful getaway surrounded by nature. It’s on 180 acres with walking trails. The vibe is unbeatable. You will find your peace. Hike! Relax in nature! Way up in the Baraboo bluffs and right by some of Wisconsin's favorite attractions. Minutes away from Devil’s Lake, ski hills and great hiking. Relax by the fire surrounded by nature. Nature therapy! Forest, wildflowers, and peacocks right out your window. Dogs allowed with prior approval but no other pets

Oct 1 – 8

G$51,471 GYD per night

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 246 reviews

The Bower- Peaceful farm stay getaway.

Thank you for checking out The Bower at Arbor Crest Acres! We would be happy to host you! This is our 5th year hosting and our 2nd tiny cottage. Our farmette is conveniently located 2 miles from town, set off the road, and through the woods. The Bower is just inside our property on the edge of the woods. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Nov 17 – 24

G$20,067 GYD per night

Guest favorite

Guest suite in Madison

4.94 out of 5 average rating, 325 reviews

Far Westside Home Away From Home

Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, a queen size comfortable hide-a-bed sofa, a 42" HDTV, a kitchenette w/a dining room table, a mini-fridge, an elliptical, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044

May 14 – 21

G$22,496 GYD per night