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.

Guest favorite

Home in Granby

4.94 out of 5 average rating, 217 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 .

Jun 23 – 30

R3,129 ZAR per night
Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

May 3 – 10

R2,523 ZAR per night
Superhost

Apartment in West Granby

4.89 out of 5 average rating, 114 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.

Oct 31 – Nov 7

R2,816 ZAR per night

Popular amenities for Simsbury vacation rentals

Stay near Simsbury's top sights

Flamig Farm9 locals recommend
Abigail's Grille and Wine Bar14 locals recommend
Heublein Tower37 locals recommend
Simsbury Commons5 locals recommend
Plan B Burger Bar - Simsbury11 locals recommend
Millwright's Restaurant and Tavern15 locals recommend

Other great vacation rentals in Simsbury

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feb 19 – 26

R1,791 ZAR per night
Superhost

Guest suite in Windsor

4.84 out of 5 average rating, 116 reviews

Rustic Loft Apartment

Sep 21 – 28

R1,893 ZAR per night
Guest favorite

Home in Simsbury

4.98 out of 5 average rating, 85 reviews

Nature House, water view, gazebo. 2 large decks

Dec 1 – 8

R3,749 ZAR per night
Guest favorite

Guest suite in Bloomfield

5.0 out of 5 average rating, 69 reviews

Guest Suite with Private Entrance & View

Dec 3 – 10

R2,732 ZAR per night
Guest favorite

Guest suite in Bloomfield

4.91 out of 5 average rating, 68 reviews

Private Cozy Suite - Zero Fees - EV Charger

Mar 6 – 13

R1,946 ZAR per night
Guest favorite

Home in Simsbury

4.82 out of 5 average rating, 17 reviews

Simsbury Farmhouse

Nov 20 – 27

R3,018 ZAR per night
Guest favorite

Guest suite in Avon

4.89 out of 5 average rating, 57 reviews

Sprawling, Light Filled Studio Apt. with Patio

Sep 21 – 28

R2,828 ZAR per night
Guest favorite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

Oct 30 – Nov 6

R4,984 ZAR per night
Guest favorite

Guesthouse in New Hartford

4.86 out of 5 average rating, 79 reviews

Litchfields West Hill New Hartford Four Season BNB

Nov 28 – Dec 5

R1,971 ZAR per night
Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

Mar 5 – 12

R2,265 ZAR per night
Guest favorite

Apartment in Canton

4.95 out of 5 average rating, 44 reviews

River Overlook - Collinsville, CT

Aug 30 – Sep 6

R3,409 ZAR per night
Guest favorite

Farm stay in Glastonbury

5.0 out of 5 average rating, 50 reviews

Historic Farmhouse by the River (Duplex)

Nov 5 – 12

R2,404 ZAR per night

Quick stats about vacation rentals in Simsbury

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

2K reviews

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 20 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 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with free parking, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Simsbury have a kitchen?

    Absolutely! We offer over 20 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 20 house rentals with free parking in Simsbury. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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  3. Connecticut
  4. Hartford County
  5. Simsbury