Simsbury Holiday Rentals

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Holiday Rentals in Simsbury

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Lux Boutique Large Private LOFT Pratt St Hartford

9.0 out of 10, Wonderful, (17)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
The price is AU$302
includes taxes & fees
1 Aug - 2 Aug
Lux Boutique Large Private LOFT Pratt St Hartford

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is AU$243
includes taxes & fees
28 July - 29 July
PICON COZY

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (1)
The price is AU$260
includes taxes & fees
27 July - 28 July
Cozy apartment in charming Hartford with AC, WiFi

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.0 out of 10, (11)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (31)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is AU$504
includes taxes & fees
31 July - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

2.0 star property
10.0 out of 10, Exceptional, (1)
"I'd like to say that upon arriving the house was beautiful. There's a gorgeous backyard pond with a water spout in the middle. A nice accessible driveway and a cute little cobblestone walkway leading up to the entrance of the guest house. It was beautiful when we arrived inside. House was clean and inviting and there was also cold water and refreshments. Will 100% be booking again... I would give it a hundred stars if I could. Best experience ever."
Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is AU$813
includes taxes & fees
28 July - 29 July
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (8)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.0 out of 10, Wonderful, (6)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is AU$249
includes taxes & fees
3 Aug - 4 Aug
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (2)
"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."
The price is AU$337
includes taxes & fees
28 July - 29 July
Modern Condo|DWNTN Hartord| XL Center| GYM

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is AU$256
includes taxes & fees
25 July - 26 July
HOMEY HOMEY

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is AU$557
includes taxes & fees
27 July - 28 July
Big farmhouse in the foothills of the Berkshires

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (34)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (30)
"We had the best time with the farm animals, great pool and unbelievable views"
Mountaintop Horse Farm with Heated Pool

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is AU$489
includes taxes & fees
4 Aug - 5 Aug
Tranquil Litchfield Connecticut Retreat".

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

9.4 out of 10, Exceptional, (21)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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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Top Simsbury Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Simsbury?

Yes, there are holiday rentals close to the most popular sights in Simsbury, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Simsbury has a good selection of restaurants. Make sure you have time to check out the forests and riverfront during your trip.

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

PICON COZY: This holiday home rental outside of Simsbury has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Simsbury?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Simsbury stay.

What’s there to see and do in Simsbury?

Cultural attractions include Performing Arts Center at Simsbury Meadows, whereas Farmington River is a spot to enjoy nature. While here, Rosedale Farms & Vineyards and Talcott Mountain State Park are other places worth a visit.

What’s a holiday rental in Simsbury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simsbury. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.