Best Vacation Homes in Simsbury
Apartment
10.0(81 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $131/Night
7 Nights - US $919
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
16145.86 ft²
- Fireplace/Heating
View
Breakfast
Pet Friendly
US $498/Night
7 Nights - US $3,488
Bed & Breakfast
9.2(1003 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
- Breakfast
US $200/Night
7 Nights - US $1,399
House
10.0(62 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $297/Night
7 Nights - US $2,082
House
8.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
9687.52 ft²
- Fireplace/Heating
- View
- Breakfast
- Pet Friendly
US $661/Night
7 Nights - US $4,628
Apartment
10.0(44 Reviews)
1 Bedroom
1 Bath
2 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $195/Night
7 Nights - US $1,363
House
10.0(34 Reviews)
2 Bedrooms
1 Bath
4 Guests
2050 ft²
- Fireplace/Heating
- Pool
Ocean View- Balcony/Terrace
US $375/Night
7 Nights - US $2,622
House
10.0(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
1650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $278/Night
7 Nights - US $1,949
Simsbury Luxury Rentals
House
10 Bedrooms
6 Baths
20 Guests
30138.95 ft²
- Fireplace/Heating
- View
- Breakfast
- Pet Friendly
US $1,837/Night
7 Nights - US $12,859
House
10 Bedrooms
6 Baths
20 Guests
30138.95 ft²
- Fireplace/Heating
- View
- Breakfast
- Pet Friendly
US $1,683/Night
7 Nights - US $11,783
House
1 Bedroom
1 Bath
1 Guest
- Pet Friendly
Internet
Child Friendly
Security/Safety
US $1,438/Night
7 Nights - US $10,063
US $1,383/Night
7 Nights - US $9,683
US $1,383/Night
7 Nights - US $9,683
New
House
10 Bedrooms
5 Baths
16 Guests
- Pet Friendly
Air Conditioner- Internet
- Child Friendly
US $1,130/Night
7 Nights - US $7,913
House
10.0(2 Reviews)
5 Bedrooms
5 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,080/Night
7 Nights - US $7,560
House
10 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,016/Night
7 Nights - US $7,114
Simsbury Pet Friendly Vacation Rentals
House
8.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $533/Night
7 Nights - US $3,728
Apartment
1.0(1 Review)
3 Bedrooms
2 Baths
4 Guests
1420.84 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $266/Night
7 Nights - US $1,862
Apartment
6.2(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $225/Night
7 Nights - US $1,575
House
5 Bedrooms
3 Baths
10 Guests
16145.86 ft²
- Fireplace/Heating
- View
- Breakfast
- Pet Friendly
US $935/Night
7 Nights - US $6,548
Apartment
6.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $205/Night
7 Nights - US $1,437
House
6.0(3 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $228/Night
7 Nights - US $1,599
House
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $158/Night
7 Nights - US $1,108
House
10.0(5 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $564/Night
7 Nights - US $3,950
Simsbury Large Vacation Homes
New
House
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $376/Night
7 Nights - US $2,632
House
5 Bedrooms
3 Baths
10 Guests
16145.86 ft²
- Fireplace/Heating
- View
- Breakfast
- Pet Friendly
US $1,010/Night
7 Nights - US $7,071
House
9.0(6 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $570/Night
7 Nights - US $3,991
House
8.4(7 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $718/Night
7 Nights - US $5,028
House
8.0(3 Reviews)
10 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $979/Night
7 Nights - US $6,854
House
7.6(4 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $572/Night
7 Nights - US $4,005
House
5 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $434/Night
7 Nights - US $3,035
New
House
6 Bedrooms
3 Baths
7 Guests
Hot Tub- Pet Friendly
- Air Conditioner
- Internet
US $609/Night
7 Nights - US $4,263
Why Choose Rent By Owner for your Simsbury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Simsbury Vacation Rentals
Where are the best neighborhoods to stay in Simsbury?
When exploring the charming neighborhoods of Simsbury, Connecticut, you’ll discover a variety of inviting areas that cater to different preferences. Whether you're seeking a peaceful retreat amidst scenic landscapes or a lively community close to local amenities, each neighborhood offers a unique atmosphere perfect for your stay. Located in the heart of Connecticut’s picturesque countryside, these neighborhoods provide an ideal base for enjoying all that Simsbury has to offer. Booking a vacation rental in this region ensures a comfortable and reliable experience, making it easy for you to relax and explore at your own pace.
Simsbury Center
In the heart of the region, this neighborhood offers convenient access to local amenities and a welcoming atmosphere. Staying here allows you to enjoy the charm of the area while being close to key attractions and scenic spots.
View 98+ Rentals in Simsbury CenterBest Times to Visit Simsbury
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region’s shoulder seasons when the weather is mild and attractions are less crowded, giving you an ideal opportunity to enjoy all that this destination has to offer.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll experience the region at its liveliest, making it ideal for outdoor activities and exploration.
Average Temperature Daytime: around 80°F - Nighttime: around 60°F
Fall (September to November)
The vibrant fall foliage draws visitors seeking scenic beauty and outdoor adventures, creating a lively atmosphere in this destination.
Average Temperature Daytime: around 70°F - Nighttime: around 50°F
Off-Season Highlights
Winter (December to February)
With colder weather and fewer visitors, winter offers a peaceful retreat for those looking to enjoy quiet moments and seasonal charm.
Average Temperature Daytime: around 40°F - Nighttime: around 25°F
Early Spring (March to April)
As nature begins to awaken, early spring presents a quieter time to enjoy the area's natural beauty with fewer tourists around.
Average Temperature Daytime: around 50°F - Nighttime: around 35°F
Weekly Weather Forecast for Simsbury
How to Book Your Simsbury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Simsbury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor spaces with a private backyard or garden area for relaxation and activities.
- Take advantage of a spacious patio or deck ideal for outdoor dining and entertaining guests.
- Make the most of scenic views from a balcony or veranda overlooking the region's natural beauty.
- Benefit from access to a swimming pool, perfect for cooling off during warm summer days in the area.
- Explore nearby walking trails or paths directly from your rental for outdoor adventures in the region.
- Utilize outdoor grilling facilities to prepare meals while enjoying the fresh air here.
- Unwind in a well-maintained yard or lawn area suitable for picnics, games, or leisure time in the area.
Top Attractions Around Simsbury
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities such as hiking, boating, and exploring scenic parks, all conveniently accessible from your nearby vacation rental in Simsbury.
Family Activities
- Talcott Mountain State Park: Explore scenic hiking trails and enjoy panoramic views of the region, perfect for family outdoor adventures.
- Simsbury Historical Society Museum: Discover local history through engaging exhibits that offer an educational experience for children and adults alike.
- Bartholomew's Cobble: Visit this unique natural area featuring diverse plant and animal life, ideal for family nature walks and discovery.
- Weatogue Park: Spend quality time in this welcoming park with playgrounds and open spaces, making it a great choice for family picnics and relaxation.
Adult Activities
- Spa and Wellness Centers: Indulge in relaxation at local spas that offer rejuvenating treatments, perfect for unwinding after exploring the scenic surroundings.
- Golf Courses: Play a round at the region’s renowned golf courses, providing a leisurely way to enjoy the area's beautiful landscapes and well-maintained greens.
- Hiking Trails: Discover the area’s natural beauty through scenic hiking trails that cater to all skill levels, offering breathtaking views and outdoor adventure.
- Local Art Galleries and Shops: Explore artisan galleries and boutique shops here, where you can appreciate regional craftsmanship and find unique souvenirs.
Other Places to Stay in Simsbury, CT
Simsbury Center
Phelps Tavern Museum
Performing Arts Center at Simsbury Meadows
Talcott Mountain State Park
Rosedale Farms & Vineyards
Simsbury Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Seasonal Activities: Take advantage of the area's seasonal events and outdoor activities by booking your accommodations well in advance to ensure availability during peak times.
- Explore Local Dining Options: Discover local eateries and farm-to-table restaurants that showcase regional flavors, adding a memorable culinary experience to your stay.
- Utilize Nature Trails and Parks: Maximize your outdoor adventures by exploring nearby parks and walking trails, which are easily accessible from most vacation rentals here.
- Connect with Community Events: Check local calendars for festivals or community gatherings during your visit to immerse yourself in the area's vibrant culture and make the most of your trip.
Transportation Options
- Connecticut Transit Bus Service: You can rely on the regional bus network to access key areas within this charming destination and connect to nearby cities effortlessly.
- Simsbury Center Taxi Services: Local taxi companies offer convenient transportation options for exploring the region or reaching your vacation rental with ease.
- Car Rentals at Bradley International Airport: For flexible travel around the area, renting a vehicle at the nearby airport provides independence during your stay.
- Bike Share Programs and Trails: Explore the scenic surroundings of the region on well-maintained bike paths suited for leisurely rides and outdoor adventures.
Local Customs Options
- Local Craftsmanship: You’ll notice a deep appreciation for handmade goods and local artisans reflecting the area's rich craft traditions.
- Seasonal Celebrations: Participating in seasonal festivals when you stay here offers a glimpse into the community’s cherished customs and holiday traditions.
- Farmers' Market Traditions: Visiting the region's farmers' markets allows you to experience the local commitment to fresh, farm-to-table produce.
- Historical Appreciation: Respect for history is evident through the preservation of historic sites and local storytelling that highlights the area's heritage.
Simsbury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Simsbury?
There are a lot of options in Simsbury. If you plan on staying in the Simsbury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Simsbury:
- Spacious Guest Apartment in the quiet suburbs of Hartford
- Cozy house with waterfall view!
- Cozy Apartment in Private, Wooded Hillside Home Enjoy Biking, Hiking, Kayaking
- Farm Stay with Horses & Pool with Mountaintop Views
- Historic Farmhouse in Northwest Connecticut. Fishing on the Farmington!
- Recently Updated, One Level, Attached Garage, Peaceful, Zen-Minimalist Space.
- Sunny, vintage farmhouse in the center of quintessential New England farm town.
- Stylish Townhome | Perfect for Family Gatherings & Events
- The Majestic View/Luxury Stay Gulf Course Views/4-Bedroom House
- Mint restored historic Simsbury 4BR estate; optional 1BR apt; all new amenities
2. How many vacation rentals have private pools in Simsbury?
There are 4 vacation rentals with private pools near Simsbury. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Simsbury are best for families?
If you are looking for a family-friendly vacation home in Simsbury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Simsbury:
4. How many Rentbyowner vacation rentals are available in Simsbury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 107 in the Simsbury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Simsbury.
5. What is the cancellation policy for a vacation rental in Simsbury, Connecticut?
Cancellation policies vary by listing; it's best to review the specific property's policy details on the listing page or contact the property owner directly to understand the terms and any applicable fees.
6. How do I secure my booking for a vacation rental in Simsbury, Connecticut?
Bookings are confirmed after completing the reservation process outlined on the listing. Be sure to read the host's instructions carefully and reach out to the owner if you have any questions before finalizing your reservation.
7. Are there any house rules I should know before staying in a rental in the area?
Yes, each property has its own set of house rules detailed in the listing. Review these guidelines prior to booking to ensure a comfortable stay and adherence to the host's expectations.
8. What amenities can I expect in a vacation rental here?
Amenities vary between properties, so check the individual listing for details. Typical features include Wi-Fi, parking, kitchen facilities, and sometimes outdoor spaces or laundry options.
9. How close are the rentals to local attractions or essential services?
Most listings indicate their proximity to key locations such as grocery stores, restaurants, and transportation links. For specific distances and accessibility, consult the property description or contact the owner directly.
Simsbury Top Rated Vacation Rentals
Other
10.0(11 Reviews)
3 Bedrooms
2 Baths
7 Guests
1853 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $292/Night
7 Nights - US $2,044
US $293/Night
7 Nights - US $2,052
Hotel
8.8(441 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $175/Night
7 Nights - US $1,225
US $405/Night
7 Nights - US $2,833
US $181/Night
7 Nights - US $1,266
Hotel
8.4(39 Reviews)
3 Baths
516.67 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $376/Night
7 Nights - US $2,630
Hotel
8.2(198 Reviews)
8 Baths
312.15 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $278/Night
7 Nights - US $1,943
Villa
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
3960 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $626/Night
7 Nights - US $4,379
