
Holiday rentals in Wolcott
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Top-rated holiday rentals in Wolcott
Guests agree: these stays are highly rated for location, cleanliness and more.

Amazing views of the Brass City
East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.
4.96 out of 5 average rating, 162 reviews
Private King suite w/ separate entry-Walk to Taft!
Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.
4.98 out of 5 average rating, 102 reviews
Amazing Paradise, Seasonal Pool, BBQ, Pool Table.
This is the private upstairs unit of our home. My family lives in the completely separate downstairs unit. You will have your own private entrance, exclusive access to the fenced backyard, seasonal inground pool, patios, and all outdoor amenities. We respect our guests' privacy. Welcome to GParadise, a quiet retreat featuring a fenced seasonal inground pool (officially open on Memorial Day. It's perfect for families, friends, wedding preparations, remote work, extended stays, romantic escapes.
4.95 out of 5 average rating, 73 reviews
Come and enjoy the BURY's of CT!
Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.
4.95 out of 5 average rating, 106 reviews
Modern cozy, pet friendly
Kick back and relax in this calm, stylish space. This is a full finished apartment with a private entrance full bathroom full one bedroom full kitchen, second bed-sleeper sofa in the living room. This is a private property we live upstairs. very safe clean neighborhood. Property sits on a 3.5 acres. From parking to the entrance is a short walk thru the grass yard. protect you trip in case of unexpected events that may require cancellation. Travel insurance can be purchased thru Airbnb .
4.86 out of 5 average rating, 96 reviews
Connecticut Chalet: Summer Retreat on 5 Acres
Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.
4.94 out of 5 average rating, 150 reviews
Cozy Oasis, Lakefront with Stunning Sunset Views
It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits! Pet friendly!
4.94 out of 5 average rating, 152 reviews
Charming 3BR Hill House *Remodeled* w/Arcade
The Lindan Hill House is a perfect AirBnb balance of luxury and value! Stay and play as you enjoy our 5 Star remodeled charming home in Terryville. This quaint and comfy home has everything you need to enjoy your stay including 3 BR with a King/Queen/2 Twin beds with premium bedding. The cozy remodeled basement is perfect for popcorn and movies, dinner and drinks at the bar, and has a game/arcade room with foosball, checkers/chess, and tons of board games! See below for a video tour.
4.95 out of 5 average rating, 137 reviews
Stylish & Luxurious 3 BDR home with Play Station
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with a 2-car garage, ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!
4.84 out of 5 average rating, 121 reviews
Relax by the water in a 4 bedroom house
Relax with the whole family at this recently renovated, spacious 4 bedroom house on Beaver Pond. Centrally located in the crossroads of Connecticut and a short train ride away from NYC, come relax by the water in a quiet neighborhood setting. Stay home and enjoy a kayak or canoe on the pond or visit the many nearby attractions like mini golf, skiing, hiking or the rest that Connecticut has to offer. The home has been recently remodeled and has a very spacious yard.
4.82 out of 5 average rating, 142 reviews
Relaxing Lake House Retreat | Family Friendly
Wake up to peaceful lake views, coffee in hand, and nowhere you need to be. This 3-bedroom lakefront retreat is perfect for relaxing getaways, family trips, or weekends with friends. Enjoy an open-concept living space, entertainer’s kitchen, spacious bedrooms, and a lake-facing porch ideal for morning coffee or sunset dinners. Whether you're spending the day on the water or unwinding indoors, this home is designed for slowing down, reconnecting, and making memories.
4.89 out of 5 average rating, 28 reviews
Cozy Family Home - Kid & Pet Friendly
3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.
4.92 out of 5 average rating, 241 reviewsPopular amenities for Wolcott holiday rentals
Other great holiday rentals in Wolcott

Cozy Waterfront Lake House
4.96 out of 5 average rating, 73 reviews
Lakefront Getaway • Hot Tub, Decks, Fires & More
5.0 out of 5 average rating, 26 reviews
Ideal for sightseeing or long stays.
4.86 out of 5 average rating, 14 reviews
KG Comfortable living.
4.86 out of 5 average rating, 80 reviews
1,500 sq feet one level ranch completely remodeled
4.8 out of 5 average rating, 20 reviews
Steele Brook Manor
4.95 out of 5 average rating, 59 reviews
Lakefront Retreat | Hot Tub + Summer Fun
4.91 out of 5 average rating, 80 reviews
Two Bedroom Apartment on Forestville Bristol
4.97 out of 5 average rating, 72 reviewsDestinations to explore
- Yale University
- Mohegan Sun
- Six Flags New England
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Sunken Meadow State Park
- Soundview Beach
- Kent Falls State Park
- Bash Bish Falls State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Sherwood Island State Park
- Ski Sundown
- Orient Beach State Park
- Wesleyan University
- Splish Splash Water Park





