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, (11)
"Could not have asked for more! Property was immaculate, the entire process was easy. Hosts are friendly and very easy to communicate with. Outdoor spaces are very peaceful and relaxing. We would highly recommend this property!"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Newly renovated cottage on the lake!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is AU$551
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is AU$179
includes taxes & fees
29 Nov - 30 Nov
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (65)
"This property is a remodeled older house. With all that old house charm. It is spacious and has three bedrooms, each with a queen bed. The couch is extremely comfortable and it was great watching TV and sipping wine."
Fun Downtown Location 2nd flr

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

152 Raymond · West Hartford Center: Cozy New England Apartment

10.0 out of 10, Exceptional, (4)
"We loved this cozy apartment in West Hartford. I was visiting family with my 78 year old mother and this first floor apartment made our trip a breeze. It was a quick walk to Whole Foods, restaurant's and shops. The house was well equipped for light cooking and happy hours and everything was spotless and smelled very clean upon our arrival. The beds were comfortable and the decor was adorable. They even had chargers plugged in beside the beds. This was the cutest, best stocked vrbo I have ever...
152 Raymond · West Hartford Center: Cozy New England Apartment

Exquisite Downtown Loft Apartment

8.0 out of 10, Very good, (6)
"Will stay again"
Exquisite Downtown Loft Apartment

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (61)
"Went to the Big E for a few days, great location, 10-15 minute ride to the fair. Was perfect to come back and relax after a long day at the fair. Home was very clean and updated. Communication was great. Could use some pans that work with the cooktop. The bathroom setup was a little strange, you have to walk throught the master bedroom to get to the bathroom, so the second bedroom guest had to walk through our bedroom in the middle of the night to use the restroom. Ad states Oven, hot tub,...
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
River Overlook - Check the view from your deck!

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

comfortable home away from home

8.8 out of 10, Excellent, (8)
"Great host and a great place really close to HFD and Pratt & Whitney."
comfortable home away from home

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...
Tolland Cabin w/ Private Hot Tub & Grill!

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

9.6 out of 10, Exceptional, (4)
"This property appeared to be recently built. While the neighborhood is nice and appeared to be safe, there were not enough utensils for the 6 people in our party. I also requested the check-in code at least the night before we arrived and that did not happen. As of the morning we flew out to Hartford, I hadn't received the check in code...very frustrating. Also the only chairs to sit in were in the downstairs living room and kitchen. If you wanted to watch TV in a bedroom, your only option was...
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.0 out of 10, Wonderful, (2)
"Great property and a great location. The host was more than welcoming and very easy to communicate to. This was our second visit to this location and we plan to stay again if availability allows. "
The price is AU$896
includes taxes & fees
9 Dec - 10 Dec
A “Wow” Experience everywhere there is something to stimulate your mind Interest
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.
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Other types of properties in West Simsbury you may be interested in

The Capitol Hotel, Ascend Hotel Collection

3.0 star property
7.4 out of 10, Good, (943)
"Great for the middle of a city and affordable. Room was larger than expected and was clean. Bathroom was pretty good and clean. The staff was AMAZINGLY nice and happy. I will return when I go to Xfinity for concerts!!"
The price is AU$133
includes taxes & fees
22 Dec - 23 Dec
The Capitol Hotel, Ascend Hotel Collection

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1255)
"Fun"
The price is AU$285
includes taxes & fees
1 Dec - 2 Dec
MGM Springfield

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1187)
"The hotel was nice. Stuart at check in was very helpful and friendly. Good breakfast options. Can’t beat the hot and gooey cinnamon rolls. Comfy bed and good location. We would stay again. "
The price is AU$198
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Southington, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.

What are some of the best holiday rentals that West Simsbury has to offer?

Tranquil Litchfield Connecticut Retreat".: This holiday home rental outside of West Simsbury is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Talcott Mountain State Park and Farmington River 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.