West Simsbury Holiday Rentals

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Holiday Rentals in West Simsbury

Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (7)
"excellent"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Fun Downtown Location
9.8 out of 10, Exceptional, (49)
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
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NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, (2)
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (15)
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, (8)
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is NZ$617
includes taxes & fees
30 Jun - 1 Jul
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Massive 5 Bedrooms: 3King 2Queen
The price is NZ$1,241
includes taxes & fees
5 Jun - 6 Jun
Massive 5 Bedrooms: 3King 2Queen
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (122)
"Loved the entire experience."
The price is NZ$586
includes taxes & fees
24 Jun - 25 Jun
Big farmhouse in the foothills of the Berkshires
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
10.0 out of 10, Exceptional, (83)
"This Highland Lake property was magical with its beyond beautiful fall colors rising above the lake & into the hills above. Our friends stated over & over “this place is better than we ever expected”!! A few of my friends commented several times how relaxing it felt to be by the lake & wake up to its beauty every morning! It was the perfect getaway for us 4 couples each having our own bedroom. The kitchen was so spacious & equipped with most everything we needed for preparing meals & dishes to...
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
comfortable home away from home
9.2 out of 10, Wonderful, (5)
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
10.0 out of 10, Exceptional, (56)
"The place was nice and is clean. I knew it was a downstairs of a house. The owner does have a dog that barks from time to time in the evening and you can hear people above, but was not too much to handle. Overall was a nice place in a nice town."
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (20)
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (11)
"The location was amazing! Although on a busy street, it was quiet and still a perfect walking distance from everything. Plenty of bars and restaurants just a few blocks away. The host was super easy to reach and the home was clean and well stocked with essentials."
Trout Brook Trail 2 · Sprawling Classic New England Home
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.4 out of 10, Exceptional, (6)
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
The getaway! Located in the downtown area.
10.0 out of 10, Exceptional, (7)
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is NZ$479
includes taxes & fees
5 Jun - 6 Jun
The getaway! Located in the downtown area.
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
9.8 out of 10, Exceptional, (44)
"Great experience over all. Would definitely recommend this cottage on the lake. Communication, check in, over all experience was great! Highly recommend!"
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
West Hartford Center Apartment
9.8 out of 10, Exceptional, (9)
"The location as it related to my trip couldn’t have been any better. The apartment was super-clean and spacious. I admire the detail on the stairway leading up to the apartment (it’s the little things👍). I will most definitely stay here again when I’m in town. Aaaaaaand that was one, humongous TV screen! Felt like I was in a movie theater!"
West Hartford Center Apartment
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See all available properties in West Simsbury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in West Simsbury you may be interested in

Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1008)
"Good stay "
The price is NZ$273
includes taxes & fees
23 Jun - 24 Jun
Holiday Inn Express Southington, an IHG Hotel
MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1012)
"We loved our room. We enjoyed the atmosphere and the casino, although we did not gamble. We loved having dinner at Costa."
The price is NZ$273
includes taxes & fees
18 Jun - 19 Jun
MGM Springfield
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (812)
"Included breakfast. Well kept up inside and out. Nice meeting room."
The price is NZ$204
includes taxes & fees
23 Jun - 24 Jun
Fairfield Inn & Suites by Marriott Springfield Enfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our West Simsbury holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up West Simsbury. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in West Simsbury. Seeing all the best attractions is bound to make you fall in love with West Simsbury. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in West Simsbury short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in West Simsbury?

Yes, there are holiday rentals in West Simsbury close to Flamig Farm, or you can select a more secluded option if you're looking for a relaxing stay. West Simsbury is known for its football games and forests. Make sure you have time to check out the riverfront while you're in the area.

How many holiday rentals will I find in West Simsbury?

Choose from 3 Expedia holiday rentals in West Simsbury for a memorable holiday.

What can I see and do in West Simsbury?

Family-friendly attractions include Flamig Farm, whereas Stratton Brook State Park is a spot to enjoy the outdoors. Six Flags New England and Performing Arts Center at Simsbury Meadows are a couple of places you'll find in the wider area.

What are holiday rentals like in West Simsbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in West Simsbury. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.

Recent reviews of West Simsbury properties
Expedia verified reviews