Simsbury Cottage Rentals
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $353/Night
For 7 Nights CA $2,468
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $197/Night
For 7 Nights CA $1,378
16145.86 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Breakfast
CA $687/Night
For 7 Nights CA $4,806
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $275/Night
For 7 Nights CA $1,928
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $442/Night
For 7 Nights CA $3,095
9687.52 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Breakfast
CA $964/Night
For 7 Nights CA $6,750
1200 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $249/Night
For 7 Nights CA $1,743
16145.86 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Breakfast
CA $1,289/Night
For 7 Nights CA $9,022
2050 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $473/Night
For 7 Nights CA $3,311
1765.28 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $620/Night
For 7 Nights CA $4,340
1650 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $384/Night
For 7 Nights CA $2,685
30138.95 ft²
20 Guests
10 Bedrooms
6 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Breakfast
CA $2,531/Night
For 7 Nights CA $17,718
People Visiting Simsbury Also Like
Why Choose Rent By Owner for your Simsbury Cottage Rentals?
What makes our Cottage 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.
Weekly Weather Forecast for Simsbury
How to Book Your Simsbury Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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 Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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
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
Frequently Asked Questions About Simsbury Rental Cottages
1. What are the top Cottages 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 Cottages 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
- Mountaintop Horse Farm with Heated Pool
- Historic Farmhouse in Northwest Connecticut. Minutes from Ski Sundown!
- 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 Cottages are available in Simsbury?
Currently, the total number of properties listed by RBO in 2026 is over 1 in the Simsbury area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Simsbury.
More Rentals You May Like Near Simsbury
5 Guests
2 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
CA $424/Night
For 7 Nights CA $2,971
30138.95 ft²
20 Guests
10 Bedrooms
6 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Breakfast
CA $2,319/Night
For 7 Nights CA $16,235
450 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
CA $434/Night
For 7 Nights CA $3,040
438 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
CA $279/Night
For 7 Nights CA $1,951
850 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $734/Night
For 7 Nights CA $5,137
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $319/Night
For 7 Nights CA $2,235
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $370/Night
For 7 Nights CA $2,590
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $382/Night
For 7 Nights CA $2,673
1 Guest
1 Bedroom
1 Bathroom
Couples Retreat
House
- Pet Friendly
- Internet
- Child Friendly
CA $1,981/Night
For 7 Nights CA $13,865
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
CA $931/Night
For 7 Nights CA $6,519
438 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
CA $563/Night
For 7 Nights CA $3,938
876 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
CA $563/Night
For 7 Nights CA $3,938
