
House holiday rentals in Simsbury
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Top-rated house rentals in Simsbury
Guests agree: These houses are highly rated for location, cleanliness and more.

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Nature Lovers Retreat-Wine Vineyards nearby
Sleeps 6! Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP , canoeing kayak rentals

WeHa Penthouse w/ Private Deck
Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Luxe Bolton Lake
Visit Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a beautiful waterfront, 3 bedrooms/3 full bathrooms and a year-round outdoor jacuzzi. Also included: gorgeous primary bedroom suite, artistic furnishings, cozy fireplace, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, kayaks, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Paradise On The Hill Luxury Apartment.
Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Prime West Hartford Center Location: Historic Gem
Discover the perfect blend of historic charm and modern comfort. Nestled in the heart of West Hartford Center, explore the vibrant Blue Back Square, just a short walk away, offering a variety of shops, restaurants, and entertainment options. The Delamar Hotel is also nearby for added convenience. Step outside onto the expansive deck, complete with a gas fire pit and grill. After each stay, the home undergoes professional cleaning, ensuring a fresh and welcoming experience.

Linny's - Lakefront Retreat Private Dock & Firepit
🌲🌳 What Guests Love -> -Private waterfront dock -Swimming and lake access -Firepit with serene views -Peaceful morning coffee spot -Family-friendly setup -Fast WiFi for remote work or streaming -Bright open living space -Comfortable bedrooms -Fully equipped kitchen -Great lake views -Smart TV and high-speed internet -Clean, modern bathroom Spend your days on the water and your evenings grilling, relaxing on the dock, or enjoying wine at sunset while the kids play lakeside.

Quiet Comfy Getaway 3 BDR home
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 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!

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!
Popular amenities for Simsbury house rentals
House rentals with a pool

3.5 Acres of Relaxation, Pool, & Cozy Charm

Casino Wine Down House w/Pool, Game Room, Big Deck

Breathtaking home with unforgettable views & pool!

Retreat with Heated Pool, 1 Mile to NYC Train

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

mid century ranch style house on farmland
Weekly house rentals

Bull Hill Bungalow

Pet Friendly Cozy Home for Work/Leisure

Home away from home

The Hangar

Island Vibes

Riverside Farm

Lake House Retreat Granby CT

Home near Six Flags/ hot tub
Private house rentals

Waterfront oasis in heart of Berkshires

Guilford Field House

Water front home with lake amenities

Berkshires Black Abbey

Private Barn Retreat Nestled In Nature

Warm 3 BR house w/ fenced yard close to everything

Spacious & serene house in Berkshires

Farmhouse Broad Brook: Comfort & Charm.
When is the best time to visit Simsbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $153 NZD | $292 NZD | $204 NZD | $204 NZD | $204 NZD | $204 NZD | $204 NZD | $204 NZD | $182 NZD | $204 NZD | $204 NZD | $153 NZD |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about house rentals in Simsbury

Total holiday rentals
Explore 10 holiday rentals in Simsbury

Nightly prices starting at
Simsbury holiday rentals start at $119 NZD per night before taxes and fees

Verified guest reviews
Over 1,180 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Simsbury holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Simsbury rentals

4.6 Average rating
Simsbury stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Mohegan Sun
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Ski Sundown
- Mount Southington Ski Area
- University of Connecticut
- Naumkeag
- Millbrook Vineyards & Winery
- Norman Rockwell Museum
- Berkshire Botanical Garden
- Hancock Shaker Village
- Smith College





