Holiday houses in West Point

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Top-rated holiday rentals in West Point

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a rustic studio retreat showcases wooden siding illuminated by warm lights at dusk. Large windows offer glimpses of the cozy interior, while kayaks are hung on the side. Surrounding greenery creates a natural ambiance, with a gravel path leading to the entrance.
Guesthouse in Mount Horeb
4.96 out of 5 average rating, 657 reviews

Cool, Roomy, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Good dogs in your reservation must be leashed outside, kenneled when you’re away.

Top Guest favourite
A spacious living area features wooden paneling and a ceiling fan. A large flat-screen television is positioned on a media console, while a decorative plant adds a touch of greenery. Large windows provide ample natural light and views of the outdoor space.
Home in Lodi
4.98 out of 5 average rating, 58 reviews

Oasis on 188 - Lake House, Kayaks, Ski Hills!

Beautiful, spacious fully remodeled 4 bedroom house with kid friendly amenities, bonus game room, and large pier. Fun outdoor space complete with a large patio and firepit. Includes a 3-season porch to relax and take in the amazing lake views. Excellent shoreline with a flat bottom to enjoy all water activities. 2 kayaks included. Walking distance to the Merrimac Ferry and extremely close to the best restaurants/bars. Pets welcome. Master bed and bath on first story. Life is better at the lake!

Top Guest favourite
A quaint gray house features a dark front door framed by two windows with flower boxes. A stone path leads to the entrance, surrounded by lush green grass and shrubs. The home's simple design is complemented by a picturesque backdrop of leafy trees.
Home in Baraboo
4.96 out of 5 average rating, 156 reviews

Cottage Near Devil's Lake

Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

Guest favourite
A spacious cabin is pictured against an expansive lawn, surrounded by verdant trees. A stone chimney rises prominently against the sky, which is covered with a mix of soft clouds and a hint of sunlight. The serene landscape evokes a sense of tranquility.
Cabin in Merrimac
4.93 out of 5 average rating, 111 reviews

Enjoy a secluded cabin with epic sunsets & horses

An enticing retreat nestled in the heart of Wisconsin’s hidden gems. 3 miles from Devil’s Lake State Park, plenty of local eateries nearby, and Devil’s Head Ski Resort located across the street. There’s no shortage of opportunities for family time & adventure. Wisconsin Dells is 20 minutes away. Bring the whole family to this spacious getaway, located on a horse ranch in the quiet, secluded area of Merrimac, WI. Take the ferry for ice cream, and fish off the dock for a fresh, relaxing dinner.

Top Guest favourite
A cozy outdoor space is featured with a wooden pergola providing shade, surrounded by blue siding. Seating includes two cushioned chairs and a swing chair, all arranged around a fire table set on a patterned rug, enhancing the inviting atmosphere.
Guest suite in Madison
4.95 out of 5 average rating, 428 reviews

Cottage Suite + Jacuzzi Bathtub & Sauna

This Suite is perfect for 1-5 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash

Superhost
A well-lit living area features a spacious sofa adorned with various throw pillows, complemented by a round coffee table. Two armchairs and ottomans provide additional seating, while natural light filters through the large windows dressed in soft curtains, enhancing the room's inviting feel.
Cabin in Merrimac
4.84 out of 5 average rating, 25 reviews

Cabin on the Peninsula with Wood Sauna

Nestled near two public access points to Lake Wisconsin including a secluded beach, the Cabin on the Peninsula offers a peaceful respite in one of the most beautiful areas in the Midwest. Watch the bald eagles and sunsets. The cabin is a few miles away from the southern entrance of Devil's Lake State Park and the Devil's Head Ski and Golf Resort. Within 30 miles to 4 ski resorts! The stylish and cozy interior offers sleeping on 3 beds and a pull out couch bed with a full kitchen and bathroom.

Guest favourite
A spacious concrete patio features a dining table with metal chairs, framed by tall trees. The American flag flutters gently in the breeze, with a serene lake view visible in the background as the sun sets, casting warm light across the scene.
Cottage in Lodi
4.9 out of 5 average rating, 68 reviews

Sunset Cottage at Lake Wi. Newly Remodeled!!!

Cozy up to this family friendly 1950's 3 Br. vintage cottage recently remodeled from top down! Relax with panoramic lake views of Lake Wi. from the cottage or patio! We are central to many hot spots within 30 mins! Devils Lake, Wisc. Dells, Wineries, Breweries, and authentic Wisc. Supper Clubs! Full reno offers amenities and technology in each room. Wood fireplace to keep you cozy in the cold months, patio with fire ring in the warm months. Seasoned firewood is included! Games! Wine! BBQ!

Top Guest favourite
An open-concept living space is captured, featuring a modern kitchen, a dining table, and a stone fireplace. The cozy seating area invites togetherness. An inviting hot tub sits on a covered deck, surrounded by trees. A sauna made of warm wood offers an additional relaxation option.
Cabin in Baraboo
5 out of 5 average rating, 103 reviews

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private

Nestled in the country, this luxurious home offers a serene escape from the hustle of city life. Enjoy two spacious bedrooms and two meticulously designed bathrooms featuring indulgent amenities, such as a deep soaking tub. A cozy living area with a stone fireplace invites relaxation, while a gourmet kitchen beckons culinary adventures. Outside, soak in the hot tub, grill up some dinner, share stories around the fire, or watch the sunset from the sauna, all amidst nature's embrace.

Top Guest favourite
A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.
Guesthouse in Sun Prairie
4.98 out of 5 average rating, 399 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Top Guest favourite
The open living area features a light-colored sectional sofa and a coffee table at its center. A dining table with wooden chairs is visible on one side, while a kitchen with modern appliances and green accents can be seen in the background. Natural light illuminates the space through large windows.
Apartment in Cross Plains
4.98 out of 5 average rating, 61 reviews

Historic Luxury Apartment

This luxury 2-bedroom 2nd floor apartment is nestled in a beautifully remodeled historic building originally built in 1860. Combining old-world charm with modern amenities, this apartment offers the perfect blend of comfort and convenience. Located right on the Main Street of Cross Plains, WI, just 25 min away from UW hospital and 35 minutes from downtown Madison. Perfect for families, professionals and anyone looking for a stylish, comfortable stay close to Madison, WI.

Guest favourite
Cabin in Merrimac
4.92 out of 5 average rating, 265 reviews

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

Guest favourite
A cozy nook features a large window adorned with a stained glass design, allowing natural light to fill the space. A plush armchair sits beside a simple blue table, while a window seat is decorated with soft cushions, inviting relaxation in a wooden interior.
Cabin in Baraboo
4.97 out of 5 average rating, 390 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

Popular amenities for West Point holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Columbia County
  5. West Point