
Holiday houses in Simsbury
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Simsbury
Guests agree: these stays are highly rated for location, cleanliness and more.

Cozy Studio Near Schools, Restaurants, and Shops
Cozy and private studio apartment in West Hartford. Location only a few minutes away from local restaurants and retail community. Off street parking. Queen size bed, small couch, small kitchen area with an island and seating for two, and small washer and dryer in the unit. This is a ground floor unit with some common hallways - noise is possible. Convenient and wonderful space for a simple, quiet, and comfortable stay. No pets allowed. Unit not suitable for children. Background check mandatory.

Sprawling, Light Filled Studio Loft with Patio
Large, light filled, spacious loft that is a converted artist studio. Floor to ceiling windows! Loft/studio is located on beautifully landscaped grounds in carriage house adjacent to main house with its own separate private entrance. Close to shopping, restaurants, canoeing, kayaking, fishing; all are very nearby. A great place to stay while visiting Avon Old Farms or Fisher Meadows Park. Conveniently close to Avon Town Center, Whole Foods, West Hartford nightlife, Farmington and 84 highway.

River Overlook - Collinsville, CT
Spotless new 1 BR apt (with additional pullout couch in LR)in downtown Collinsville, perched across the street from Farmington River and Rails to Trails. Steps to Collinsville - restaurants, antiques, concerts, walking, biking, fishing, canoe/kayaking. Sleeping for 4 (queen bed in BR, and pullout couch in LR). Relax on your private deck overlooking the river. See if you can spot our local Bald Eagle family! Voted one of "America's 10 Coolest Small Towns" by Frommer's Budget Travel Magazine!

Apt near Big E, Six Flags, Bradley airport
Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Newly Renovated Apartment
Welcome to Center Street Stay, your charming retreat in Simsbury, CT. This fully renovated, first-floor one-bedroom apartment blends modern comfort with convenience. The kitchen is equipped with modern appliances, perfect for culinary endeavors. Relax in the cozy living area with a smart TV or get some rest on the memory foam queen mattress. The renovated bathroom offers sleek fixtures and a rejuvenating shower. Enjoy amenities like in-unit washer/dryer, high-speed Wi-Fi, and free parking.

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug
A private cozy suite for you! Better than a hotel or private room & less than an entire house. We do not charge extra fees! Sizable discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Heating, cooling and hot water are all-electric. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. EV charger!

Peaceful Meadow Retreat
Unwind at Meadow's Edge, a serene and cozy refuge where you can come to relax and recharge! Looking out on our peaceful meadow and abutting 125 acres of corn fields, this is a perfect spot to enjoy a book on the shaded back patio, a yoga or meditation session, or a quiet walk through the fields & woods. Take in the view from inside the southern facing windows, where it is not uncommon to see wildlife at dawn or dusk. This is the tranquil getaway that you have been waiting for!

Relax By The Water
Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

Guest Suite with Private Entrance & View
Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Bloomfield Bungalow
This is a unique apartment that was once a dentist office. It features a stylish décor and it is well appointed with everything needed to make your stay comfortable! Bloomfield is a quintessential New England small town. This apartment is located steps away from the Bloomfield Town Hall and the town green. The area is perfect for peaceful walks. There are fantastic restaurants in walking distance in this beautiful community.

Collinsville Overlook at LaSalle
Stay in the heart of Collinsville, above the historic Lasalle Market. Just steps to the Farmington River, Rails to Trails, restaurants, shopping, antiquing, concerts, walking, biking, fishing, canoeing and kayaking. Sleeping for 4 (including a queen bedroom and a queen air mattress). Enjoy breakfast in your private nook overlooking the village. Voted one of America's 10 Coolest Small Towns by Frommer's Budget Travel Magazine!

Windy Top Cottage ~ A Romantic "European" Getaway
The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!
Popular amenities for Simsbury holiday rentals
Other great holiday rentals in Simsbury

BoHo Bedroom w/Private Bathroom

Authentic Mid-century modern

Private room “A” in Hartford

Sunny upper room #8

Simple living in Suffield

Home away from home 3

A cozy family home in a quiet area

Understanding Room @ The Lighthouse - 2nd floor
When is the best time to visit Simsbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $229 AUD | $201 AUD | $213 AUD | $192 AUD | $213 AUD | $213 AUD | $236 AUD | $227 AUD | $232 AUD | $229 AUD | $229 AUD | $215 AUD | 
| 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 holiday rentals in Simsbury
 - Total holiday rentals- Explore 30 holiday rentals in Simsbury 
 - Nightly prices starting at- Simsbury holiday rentals start at $76 AUD per night before taxes and fees 
 - Verified guest reviews- Over 2,760 verified reviews to help you choose 
 - Family-friendly holiday rentals- 10 properties offer extra space and kid-friendly amenities 
 - Pet-friendly accommodation- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 20 properties have a dedicated workspace 
 - Wi-Fi availability- 30 of Simsbury holiday rentals include Wi-Fi access 
 - Popular amenities for guests- Guests love Kitchen, Wi-Fi and Pool across Simsbury rentals 
 - 4.8 Average rating- Simsbury stays are highly rated by guests—averaging 4.8 out of 5! 
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Walnut Public Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Wildemere Beach
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Clinton Beach
- Giants Neck Beach
- Bayview Beach
- Grove Beach
- Harveys Beach
- Bushnell Park
- Brimfield State Forest
- Fort Trumbull Beach
- Hammonasset Beach State Park
- Chapman Beach
- Norman Rockwell Museum
- Bigelow Hollow State Park
