Vacation rentals in Pittsville

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Top-rated vacation rentals in Pittsville

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

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Guest favorite

Home in Schofield

4.98 out of 5 average rating, 40 reviews

Wooded waterfront retreat with hot tub & fire pit

JohnRating, 5 stars2 months ago

We went up for a ski weekend and it was the absolute perfect homebase. The kitchen was great, the beds were spacious and comfortable, and there was plenty of room for everyone to do their own thing while still being very communal. Amazingly convenient for Granite Peak and plenty of room in the garage to store heaps of gear.

Guest favorite

Home in New Lisbon

5 out of 5 average rating, 35 reviews

Retreat on the Beach! EV Friendly! Hot tub!

LuzRating, 5 stars1 month ago

Me and my family enjoyed are time at the lake house. Can’t wait to comeback and hopefully we have more time to explore the area and more activities since it was raining most of the time. Overall the house felt like home. Highly recommended this lake house. Thank you to the host for all the help.

Superhost

The cabin's outdoor deck is surrounded by lush greenery and features comfortable hanging chairs and colorful seating. Warm string lights illuminate the space, enhancing the inviting atmosphere. The modern A-frame structure stands amidst the trees, showcasing large windows that offer a glimpse of the interior.

Home in Wautoma

4.91 out of 5 average rating, 106 reviews

Lake Getaway with Escape Room, Speakeasy & Hot Tub

NicholasRating, 5 stars2 weeks ago

we love staying at Cherie's place! the escape room was alot of fun when we first arrived. the speakeasy was so cool, loved all the board games and little touches (like the pogs). the hot tub was perfect after a long day and there was plenty to do with the lake stuff\fireworks pit. we will definitely be staying again when possible

Superhost

An inviting entrance is framed by log pillars supporting a wooden awning. The door is decorated with a seasonal wreath, while two red gift boxes are positioned on either side of a welcome mat. A wooden deck and trees are visible in the background.

Cabin in Friendship

4.8 out of 5 average rating, 5 reviews

Luxury Cabin by Castle Rock Lake

DebraRating, 5 stars8 months ago

Thank you Marybeth for providing a super fun lodging experience. Your place was clean and had more than everything we needed. We loved the sauna & games you provided. The kitchen was well equipped and very conducive to gathering. Your advanced list of places and things to do in the area was super helpful! Loved the deck and fire pit. Little back story. 21 years ago we brought our beautiful daughters home from China. Our families reconnected every year but then Covid happened. This was our first “Mom’s only” weekend and let me tell you, it was beyond memorable. Thank you! ❤️

Superhost

A two-story cabin is depicted with a dark wood exterior, featuring a prominent triangular roof. Stone steps lead to the entrance, bordered by a neatly maintained lawn with scattered greenery. Nearby, another log-style cabin is partially visible, enhancing the natural setting.

Cabin in Warrens

4.93 out of 5 average rating, 27 reviews

Unique Privately Owned - Near UTV trails/waterpark

LaneyRating, 5 stars4 months ago

Natasha was very responsive. Her place had all the extras which was really nice not to have to pack, dish soap, dishwasher detergent, towels, crockpot, pots/pans, pizza cutter, etc. Very close to 3 bears, so quick walk across the street (in the resort neighborhood) to the Waterpark!

Top guest favorite

A covered porch features two lounge chairs and a small table, accompanied by a glass of water and a book. The serene view of the lake is visible through the wooden railing, with green trees surrounding the area.

Cottage in Hancock

4.98 out of 5 average rating, 56 reviews

Stone Have Lake cottage -Stunning views!

RyanRating, 5 stars1 month ago

This is a wonderful property. The small touches made it feel really wonderful. From thoughtful, welcome snacks, and popcorn to the details in the decorations. One of the most thoughtful Airbnb‘s, we’ve ever stayed in. Our kids had lots to do the garage game room was so fun. You could see every star in the sky at night would highly recommend. Thank you for such a great time.

Superhost

A spacious deck offers scenic views of the surrounding landscape and a tranquil body of water. Outdoor seating is arranged with a sectional sofa and a picnic table, inviting relaxation and gathering. Lush greenery and vibrant fall foliage frame the natural setting under a clear blue sky.

Home in Amherst

4.87 out of 5 average rating, 38 reviews

Hilltop Views & water access-20 acres!

DeAnnaRating, 5 stars1 month ago

We had a great time! We enjoyed the open concept kitchen/dinning and living room. The hot tub was nice to have. There was plenty of towels for the hot tubs as well as showering for our group. We did get to use the golf carts on Friday for a little bit since it was so nice out but Saturday the weather was crappy. All in all we had a really nice weekend away!

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Popular amenities for Pittsville vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pittsville

Guest favorite

This image captures a rustic home set along the Black River, surrounded by tall trees and a gentle sloping driveway. A large deck extends towards the water, with outdoor seating visible. The house features a combination of wood and stone elements, enhancing its natural charm.

Cabin in Black River Falls

4.94 out of 5 average rating, 36 reviews

Riverfront-Sandy Beach-TikiBar-Dock-RecRoom-3700ft

LukeRating, 5 stars2 months ago

Great home and beautiful location!

Superhost

A wooden deck is shown with a glass-top dining table surrounded by six chairs. An umbrella provides shade over the table. Sliding glass doors lead into the cabin, and blue chairs are visible in the background amidst trees.

Cabin in Friendship

4.84 out of 5 average rating, 49 reviews

Rustic Log Cabin 5 min to Castle Rock Lake

James JiangRating, 5 stars3 weeks ago

We had a fantastic time staying in this cabin, very peaceful and great for traveling with friends

Guest favorite

A treehouse elevated among tall pines features a wooden exterior with a small balcony. A ladder leads up to the entrance, while the surrounding area is filled with natural greenery, creating a serene forest setting.

Cabin in Hancock

4.95 out of 5 average rating, 422 reviews

Peaceful Wooded Sanctuary- with private dog park!

JessicaRating, 5 stars1 week ago

Emily was an excellent host. She was extremely responsive and accommodating. There was a minor issue/mix-up when I first arrived; I reached out to her and she responded almost immediately and had things resolved within a matter of minutes. The cabin has the essentials that you need but it's the outdoor space that's the real gem here. There's so much room to explore and just wander about. You can really have an adventure without even leaving the property. The place was very quiet and peaceful; very rarely did I hear any cars drive by or hear any noise from neighboring cabins. I had my dog with me and she absolutely LOVED it here. We spent most of our time outside but in the evenings and when the weather wasn't as nice, the cabin offered a comfy and cozy space for us to relax. I would definitely visit again.

Guest favorite

The exterior of the cabin is framed by tall trees, with a sloped roof and large windows reflecting the soft colors of the evening sky. A wooden staircase leads to the entrance, set against a grassy area adorned with fallen leaves.

Cabin in Westfield

4.93 out of 5 average rating, 97 reviews

Spacious A-Frame Cabin in the Woods with Dry Sauna

NicholeRating, 5 stars1 month ago

Our family enjoyed a cozy stay in this beautiful spot and hope to return again sometime!

Guest favorite

A rustic cabin is situated near the water's edge, showcasing wooden beams and a stone chimney. A sandy area is visible in front, with a small dock extending into the calm water. Trees surround the cabin, adding to the natural setting.

Cabin in Necedah

4.99 out of 5 average rating, 124 reviews

Little Cabin in the Big Woods - Cabin #2

RebeccaRating, 5 stars2 months ago

Great place. We had a lot of fun in the game room! It was a fun girls weekend.

Guest favorite

Cabin in Oxford

4.84 out of 5 average rating, 75 reviews

Lilikoi Resort LLC

AdamRating, 5 stars1 month ago

We loved our stay. From the moment we reserved the Lilikoi to our checkout, Daryl was very attentive and responsive. It blew us away on how peaceful it was there. My girlfriend’s son rode a bike for the first time without training wheels, went kayaking for his first time, and learned archery. There was a lot of wildlife and we spent most of our time around the camp fire and surrounding woods. Dog friendly trails and lodging. Do yourself a favor a book a weekend or a week. You won’t regret it.

Superhost

The log home features a sturdy wooden deck with steps leading to the entrance. A prominent stone fireplace is centered on the facade, flanked by large windows that allow natural light to fill the interior. The surrounding area is adorned with well-maintained greenery.

Cabin in Arkdale

4.9 out of 5 average rating, 293 reviews

Log Home, family friendly, hot tub, near lakes

JulieRating, 5 stars1 week ago

Debra's house has everything any family needs for fun. It is close enough to Wisconsin dells to easily spend a day there and go home for relaxation. The kitchen is well stocked to do your own meals. She was great host!

Superhost