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 favourite
Home in Granby
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 .
Nov. 20 – 27
$279 CAD per night
4.94 out of 5 average rating, 216 reviews
Guest favourite
Guesthouse in Glastonbury
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.
Apr. 25 – May 2
$263 CAD per night
4.96 out of 5 average rating, 133 reviews
Guest favourite
Home in Simsbury
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.
Dec. 25 – Jan. 1
$316 CAD per night
4.98 out of 5 average rating, 85 reviews

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 favourite
Home in Simsbury
Simsbury Farmhouse
Dec. 5 – 12
$262 CAD per night
4.82 out of 5 average rating, 17 reviews
Guest favourite
Guest suite in Bloomfield
Guest Suite with Private Entrance & View
Jul. 27 – Aug. 3
$222 CAD per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Guest suite in Bloomfield
Private Cozy Suite - Zero Fees - EV Charger
Aug. 12 – 19
$154 CAD per night
4.91 out of 5 average rating, 67 reviews
Guest favourite
Home in Simsbury
Simsbury Ranch in a quiet neighborhood!
Oct. 18 – 25
$419 CAD per night
4.89 out of 5 average rating, 57 reviews
Guest favourite
Home in Windsor
Relax By The Water
Aug. 18 – 25
$308 CAD per night
4.97 out of 5 average rating, 33 reviews
Guest favourite
Apartment in Canton
River Overlook - Collinsville, CT
Feb. 24 – Mar. 3
$292 CAD per night
4.95 out of 5 average rating, 43 reviews
Guest favourite
Guest suite in Avon
Sprawling, Light Filled Studio Apt. with Patio
Feb. 14 – 21
$237 CAD per night
4.89 out of 5 average rating, 57 reviews
Guest favourite
Farm stay in Glastonbury
Rustic Farmhouse by the River (Duplex)
Mar. 20 – 27
$189 CAD per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Bloomfield
Spacious Charming New England Cape
Aug. 24 – 31
$699 CAD per night
4.94 out of 5 average rating, 88 reviews
Guest favourite
Home in Windsor
Hilltop RiverView Retreat
Jan. 2 – 9
$452 CAD per night
4.94 out of 5 average rating, 69 reviews
Guest favourite
Cottage in Bloomfield
Hidden Vintage Waterfront Eco Cabin on a Creek
Apr. 1 – 8
$356 CAD per night
4.97 out of 5 average rating, 95 reviews
Guest favourite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a great lake!
Apr. 21 – 28
$366 CAD per night
4.96 out of 5 average rating, 28 reviews

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

Destinations to explore

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