
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.

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.

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 Skiing 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

Breathtaking home with unforgettable views & pool!
This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or star gazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. please let us know before booking more than 4 people whether it is just for the day or night or both. no loud music no parties

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.

Spacious 3 Bedroom Ranch With Office
Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

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.

Belle Meade
Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

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.

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!

Litchfield County Farmhouse with a Modern Twist
Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Idyllic family retreat - spacious lake home,
This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.
Popular amenities for house rentals in Simsbury
House rentals with a pool

The Getaway-HOST & Co.

Hilltop House w/POOL/SPA- HOST & Co.

Ezekiel's Palace 24th

Cabin Retreat with Pool and Firepit on 4 Acres

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

Cozy Getaway near Lake & Skiing

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

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Weekly house rentals

Lake Escape: Lake Cottage Charm, Lake Front, AC

Home away from home

By The River

The Hangar

Boondocks Oasis On The River

Lake House Retreat Granby CT

Cabin with Hot Tub and Lake Access

Quiet Comfy Getaway 3 BDR home
Private house rentals

Cozy Waterfront Home w/ Hot Tub Connecticut River

My Lake House w/dock and kayaks

Winter ski retreat minutes from Butternut

Clean & Quiet Home| Enclosed 3 Season Porch & Deck

Water front home with lake amenities

The Farmhouse Stay

Home near Six Flags/ hot tub

King Bed w/ Game Room near Massmutual w/ Riverview
When is the best time to visit Simsbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $116 SGD | $116 SGD | $116 SGD | $154 SGD | $154 SGD | $154 SGD | $154 SGD | $154 SGD | $137 SGD | $154 SGD | $154 SGD | $116 SGD |
| 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 20 holiday rentals in Simsbury

Nightly prices starting at
Simsbury holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 1,220 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Simsbury holiday rentals include wifi access

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

4.7 Average rating
Simsbury stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Mohegan Sun
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Mount Southington Ski Area
- Taconic State Park
- Yale University Art Gallery
- Sleeping Giant State Park
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Berkshire Botanical Garden
- Hancock Shaker Village
- University of Connecticut
- Millbrook Vineyards & Winery
- Wesleyan University




