West Simsbury Holiday Rentals

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Holiday Rentals in West Simsbury

Property grounds
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (6)
"excellent"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
The price is NZ$1,154
includes taxes & fees
21 May - 22 May
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (17)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
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Microwave, oven, stovetop, dishwasher
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
10.0 out of 10, Exceptional, (2)
"My family and I enjoyed our stay here. We had lots of space for my 4yo to run around and each of my 3 kids had their own room. The house was very clean and the host was easily able to contact if I had questions or concerns. We would def. stay here again"
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Fridge, microwave, oven, stovetop
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
10.0 out of 10, Exceptional, (5)
"From the very beginning the hosts were fantastic. There was great communication and offered support. The property was super clean , well organized, and perfect for what we needed. I will be staying here again and truly recommend it !"
The price is NZ$381
includes taxes & fees
20 May - 21 May
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Fridge, microwave, oven, stovetop
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
Outdoor pool, a heated pool
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
Fridge, microwave, oven, stovetop
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (9)
"Awesome! Check in was smooth, property was super clean and spacious. We will definitely be back!"
Trout Brook Trail 2 · Sprawling Classic New England Home
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (18)
"We had such a relaxing, wonderful stay at this lakefront oasis. The lake views from the upstairs living room & the downstairs kitchen and yard were lovely. The number of song birds was delightful to watch and hear. We counted 31 birds in <1 hour! We also saw turtles, fish, and a Bald Eagle."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
View from property
Newly renovated cottage on the lake!
10.0 out of 10, Exceptional, (14)
"Visited a local winery, Distillary & Ice Cream shop! Ate at Salt Water Grille, Met up with extended family from Mass."
Newly renovated cottage on the lake!
Fridge, microwave, oven, stovetop
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$421
includes taxes & fees
21 May - 22 May
The getaway! Located in the downtown area.
Interior
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (8)
"The location was just as promised. The view on the deck is beautiful and the apartment was clean and well stocked with anything you might need. The location is also walking distance to various shops, pizza, restaurants and bars. The river walk across the street is also great if you want to take a stroll. Carol was also great to work with. We’ll be back."
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop
New!Quaint & Convenient Hideaway: Great Location
10.0 out of 10, Exceptional, (2)
"Dress shopping with the daughters, needed to be near the Trinity Boat House wish I had found this spot before Spring of senior year!"
New!Quaint & Convenient Hideaway: Great Location
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (47)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
TV, DVD player, books, video library
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
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks
9.8 out of 10, Exceptional, (19)
"Words cannot describe how beautiful and peaceful this place was I did not wanna leave and I’m already looking forward to my next stay! Owners were wonderful to communicate, and exceeded my expectations. Thank you for giving me blissful place to spend my birthday."
Cozy Lakefront Bungalow w firepit/dock/kayaks
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.4 out of 10, Exceptional, (33)
"Very positive."
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Fridge, microwave, oven, stovetop
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
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.2 out of 10, Wonderful, (5)
"A slightly older house with some issues due to that, but the owners were absolutely wonderful and rectified any issues we faced almost immediately. The surrounding area, community, and house itself despite the age, are absolutely beautiful."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Paper towels
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!
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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

8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1001)
"I love everything the people that help in are more then a helpful, question always answer, the pool was delicious, the spa was good, showers are very clean, bed are so comfortable. And the hall experience was magnificent thanks I well do it ones more ,thanks to every staff. "
The price is NZ$272
includes taxes & fees
21 May - 22 May
MGM Springfield
Exterior
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (790)
"Wish the restaurant was open for dinner, and not sure why they want to charge you for your car. Rooms were a nice size"
The price is NZ$206
includes taxes & fees
3 Jun - 4 Jun
Fairfield Inn & Suites by Marriott Springfield Enfield
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1004)
"Clean, comfortable and great customer service! "
The price is NZ$261
includes taxes & fees
27 May - 28 May
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.

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