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Vacation rentals in Simsbury

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Top-rated vacation rentals in Simsbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cabin in Bloomfield

4.97 out of 5 average rating, 112 reviews

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary

Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

Home in Bloomfield

4.95 out of 5 average rating, 109 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods near Wintonbury Hills Golf course. Neighborhood setting and on a private corner lot. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails too! Close to Ski Sundown, Mt Tom, MGM Casino, tons of golf courses, beaches.

Home in Granby

4.95 out of 5 average rating, 242 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Clean refreshing three-bedroom , one floor living, centrally located, walk to town for fantastic dining ! Mexican, Sushi and Thai, Mediterranean, Italian, Continental, and Vegan ! 8 minutes to rt 91 and Bradley, minutes to Mass line! Downstairs living space with a gameroom and comfortable seating, and extra sofa bed and airbeds, if needed. Other than clothes, you will need nothing else...I provide everything from razors to coffee , tea and a HUGE snack basket ! Even have a heating pad .

Rental unit in West Granby

4.9 out of 5 average rating, 130 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the Joab Griffin House. We are a beautiful historic farmhouse set on a private hill tucked away in the foothills of the Berkshires, surrounded by gorgeous farmland and hundreds of acres of land trust and game refuge trails, streams, and waterfalls within a five-minute walk from your door. Enjoy a private apartment in this lovely farmhouse. Here, you'll find cool summer breezes, cozy, warm, sun-filled days, and star-filled skies with the sounds of the brook outside your window.

Home in Simsbury

4.98 out of 5 average rating, 106 reviews

Nature House, water view, gazebo. 2 large decks

Charming house with water view from large deck with attached enclosed lighted gazebo. *Master suite has queen bed TV and full bath. 2 twin beds and comfortable inflatable queen bed. Pellet stove for hassle free fires. Large eat in kitchen. Dining room seats 6. Conveniently located near Ski Sundown, Talcott Mountain State Park, Roaring Brook Nature Center, Flamig Farm, shopping, backyard has access to Onion Mountain walking trails. 2 Samsung HD TV's High efficiency washer & dryer.

Barn in Bloomfield

4.97 out of 5 average rating, 119 reviews

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Basque in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Guest suite in Bloomfield

5 out of 5 average rating, 100 reviews

Guest Suite with Private Entrance & View

Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Guesthouse in Granby

4.98 out of 5 average rating, 773 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest suite in Morris

4.99 out of 5 average rating, 379 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Cottage in Granby

4.88 out of 5 average rating, 173 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Rental unit in Winchester

4.91 out of 5 average rating, 369 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

Rental unit in Enfield

4.99 out of 5 average rating, 193 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

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Popular amenities for Simsbury vacation rentals

Free parking on premises

Air conditioning

Stay near Simsbury's top sights

Heublein Tower37 locals recommend

Talcott Mountain State Park34 locals recommend

The Shoppes at Farmington Valley18 locals recommend

Millwright's Restaurant and Tavern15 locals recommend

Abigail's Grille and Wine Bar14 locals recommend

Harvest Cafe & Bakery12 locals recommend

Other great vacation rentals in Simsbury

Home in Simsbury

5 out of 5 average rating, 11 reviews

An Oasis Where Nature & Comfort Unite

Guest suite in Granby

4.92 out of 5 average rating, 13 reviews

The Hungary Brook Stay in Granby

Home in Windsor

4.98 out of 5 average rating, 52 reviews

Relax By The Water

Home in West Hartford

5 out of 5 average rating, 30 reviews

The little house that could!

Home in Windsor

5 out of 5 average rating, 20 reviews

Quiet Comfy Getaway 3 BDR home

Guest suite in Avon

4.88 out of 5 average rating, 81 reviews

Sprawling, Light Filled Studio Apt. with Patio

Cabin in Enfield

4.96 out of 5 average rating, 46 reviews

Vintage Riverview Cottage

Farm stay in Bloomfield

4.86 out of 5 average rating, 37 reviews

Auerfarm Farmstay Baldwin Cottage (169)

Quick stats about vacation rentals in Simsbury

Total rentals
30 properties
Total number of reviews
2.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

Are there pet-friendly vacation rentals in Simsbury?
Four-legged friends are welcome in Simsbury. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Simsbury?
Yes! Work meets play with ease at over 20 vacation rentals in Simsbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Simsbury have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Simsbury?
Simsbury has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Simsbury?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Simsbury have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Simsbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simsbury have free parking?
Absolutely! We offer over 10 house rentals with free parking in Simsbury. Enjoy a tailored experience with all the comforts you desire.

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