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Cottages in Simsbury

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Enjoy a peaceful lakeside retreat with a dock, table, and chairs, surrounded by lush grass and a shaded tree.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Lakefront Tranquility/Fishermans Delight
Cozy living space with a dining area, sofa, and wooden ceiling with exposed beams.

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (19)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Westfield Vacation Rental w/ Porch, Pets Welcome!
Stylish single-story home with a gabled roof and a cozy front porch.

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Enjoy a serene lakeside view from this deck overlooking a calm body of water.

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
Modern Terryville Cottage w/ Deck & Lake View!
Enjoy meals in the fully equipped kitchen with a dining area featuring a round table and range hood.

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Modern Terryville Cottage w/ Deck & Lake View!
Enjoy meals in this well-equipped kitchen and dining area, featuring a stainless steel refrigerator, oven, and comfortable seating for four.

Modern Terryville Cottage w/ Deck & Lake View!

9.2 out of 10, Wonderful, (5)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!
Lakefront Granby Escape w/ Private Dock & Kayaks!
Cozy living room with a fireplace, sofa, and coffee table, surrounded by rustic charm.

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Reel Simple on Bolton Lake
Enjoy a peaceful retreat with a serene view of the lake and surrounding landscape from this outdoor patio.

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (25)
"We stayed here while visiting our family during a stressful time. It was wonderful to come back to this cozy quiet cottage each night."
Reel Simple on Bolton Lake
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Enjoy cooking in this well-lit kitchen with sleek cabinetry, a stainless steel range, and microwave.

Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard

10.0 out of 10, Exceptional, (1)
"Nice to have a Vrbo versus hotel in a quiet neighborhood. Heater wasn’t working and owner had someone there within a hour to fix it. We left our laptop and owner notified us immediately. Placed worked out great for our business trip."
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Relax on the outdoor patio with comfortable sofas, a table, and a chair, shaded by a stylish umbrella.

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

3.0 star property
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Guests can enjoy serene lakeside views from the comfort of their accommodations.

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

10.0 out of 10, Exceptional, (44)
"Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again! "
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Charming Farmhouse w/ Pool & Fishing Pond!
Enjoy cooking in this well-equipped kitchen with a stove, sink, and dishwasher.

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Lakefront Home, Close to Mt Southington!
Relax in this inviting space with a large table, wicker chairs, and a potted plant.

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
Wolcott Home w/ Deck: Near Connecticut Attractions
Kitchen features a stainless steel sink, microwave and oven, and dishwasher, with a decorative stained glass window above.

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Escape to a serene oasis amidst lush greenery and vibrant flowers.

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Historic Farmhouse Near Mountains & Colleges!
Relax in this inviting outdoor seating area with a comfortable sofa and coffee table.

Historic Farmhouse Near Mountains & Colleges!

3.0 star property
Historic Farmhouse Near Mountains & Colleges!
Springfield Vacation Rental: 1 Mi to Downtown
Compact kitchen with modern layout, functional design, and ample storage.

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Spacious Tolland Home w/ Deck + Screened Porch!
Interior

Spacious Tolland Home w/ Deck + Screened Porch!

3.0 star property
Spacious Tolland Home w/ Deck + Screened Porch!
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

Best Western Manchester

Best Western Manchester

10/10 Excellent
"Pet friendly sometimes means a little worn or a little dirty, but not in this case. I was very pleased with the condition of the room and the common areas. "
Mark 1-night trip
Posted 18 hours ago
Best Western Manchester