Vacation rentals in Simsbury

Find and book unique accommodations on Airbnb

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 .

Mar 1 – 8

R3,266 ZAR per night
Superhost

Apartment in West Granby

4.88 out of 5 average rating, 113 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

R2,812 ZAR per night
Guest favorite

Cottage in Windsor

4.89 out of 5 average rating, 161 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

Jun 9 – 16

R1,943 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

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

May 30 – Jun 6

R2,842 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

Oct 6 – 13

R3,744 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

Dec 3 – 10

R1,822 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

R2,728 ZAR per night
Guest favorite

Home in Simsbury

4.82 out of 5 average rating, 17 reviews

Simsbury Farmhouse

Nov 26 – Dec 3

R3,014 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

Jan 20 – 27

R2,825 ZAR per night
Guest favorite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

Oct 29 – Nov 5

R4,977 ZAR per night
Guest favorite

Home in Windsor

4.97 out of 5 average rating, 33 reviews

Relax By The Water

Nov 2 – 9

R3,851 ZAR per night
Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

Mar 5 – 12

R2,262 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

R2,401 ZAR per night
Guest favorite

Home in Bloomfield

4.94 out of 5 average rating, 87 reviews

Spacious Charming New England Cape

Sep 4 – 11

R7,967 ZAR per night
Guest favorite

Apartment in Canton

4.95 out of 5 average rating, 44 reviews

River Overlook - Collinsville, CT

Aug 29 – Sep 5

R3,404 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

  1. Airbnb
  2. United States
  3. Connecticut
  4. Hartford County
  5. Simsbury