Holiday rentals in Simsbury

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Top-rated holiday rentals in Simsbury

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

Guest favourite

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 .

1–8 Mar

$232 SGD per night
Superhost

Flat 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.

31 Oct – 7 Nov

$200 SGD per night
Guest favourite

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.

9–16 Jun

$138 SGD per night

Popular amenities for Simsbury holiday 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 holiday rentals in Simsbury

Guest favourite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

30 May – 6 Jun

$202 SGD per night
Guest favourite

Home in Simsbury

4.98 out of 5 average rating, 85 reviews

Nature House, water view, gazebo. 2 large decks

6–13 Oct

$266 SGD per night
Guest favourite

Guest suite in Bloomfield

4.91 out of 5 average rating, 68 reviews

Private Cozy Suite - Zero Fees - EV Charger

3–10 Dec

$130 SGD per night
Guest favourite

Guest suite in Bloomfield

5.0 out of 5 average rating, 69 reviews

Guest Suite with Private Entrance & View

3–10 Dec

$194 SGD per night
Guest favourite

Home in Simsbury

4.82 out of 5 average rating, 17 reviews

Simsbury Farmhouse

26 Nov – 3 Dec

$214 SGD per night
Guest favourite

Guest suite in Avon

4.89 out of 5 average rating, 57 reviews

Sprawling, Light Filled Studio Apt. with Patio

20–27 Jan

$201 SGD per night
Guest favourite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

29 Oct – 5 Nov

$354 SGD per night
Guest favourite

Home in Windsor

4.97 out of 5 average rating, 33 reviews

Relax By The Water

2–9 Nov

$274 SGD per night
Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

5–12 Mar

$161 SGD per night
Guest favourite

Farm stay in Glastonbury

5.0 out of 5 average rating, 50 reviews

Historic Farmhouse by the River (Duplex)

5–12 Nov

$171 SGD per night
Guest favourite

Home in Bloomfield

4.94 out of 5 average rating, 87 reviews

Spacious Charming New England Cape

4–11 Sep

$567 SGD per night
Guest favourite

Serviced apartment in Canton

4.95 out of 5 average rating, 44 reviews

River Overlook - Collinsville, CT

29 Aug – 5 Sep

$242 SGD per night

Quick stats about holiday 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

Destinations to explore

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