House vacation rentals in Simsbury

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Top-rated house rentals in Simsbury

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

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Guest favourite

Home in Colebrook

4.99 out of 5 average rating, 202 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Apr. 2 – 9

$391 CAD per night

Guest favourite

Home in Coventry

4.94 out of 5 average rating, 160 reviews

Cozy Cottage * Coventry Lake* 15 min to UConn *

Enjoy this quaint lake cottage that is close to Uconn and all the area has to offer. It has been updated with new flooring and fresh paint. Access to a private association beach is only a three minute walk. This beach is for paid guests only. Please note the fireplace is not a working fireplace. The area offers hiking trails, antiquing, vineyards and access to the lake. In the winter there is ice fishing and ice skating. In the summer you can kayak, paddleboard or relax on the beach.

Apr. 13 – 20

$275 CAD per night

Guest favourite

Home in Granby

4.95 out of 5 average rating, 220 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 .

Jan. 4 – 11

$321 CAD per night

Guest favourite

Home in Vernon

4.99 out of 5 average rating, 115 reviews

Luxe Bolton Lake!

Now booking for summer! Relax and savor the tranquil vistas of picturesque Middle Bolton Lake while enjoying stylish comfort in our 2000+ sq. ft. 3 bedroom/3 bathroom architecturally-designed home. Amenities include expansive waterfront, outdoor jacuzzi, gorgeous master bedroom suite w/ private en suite bath, boutique toiletries, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, wifi, large deck, fire pit, kayaks, vintage canoe and much more. Come make lasting memories.

Feb. 11 – 18

$836 CAD per night

Guest favourite

Home in Chester

4.96 out of 5 average rating, 311 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Dec. 7 – 14

$296 CAD per night

Guest favourite

Home in Ware

4.89 out of 5 average rating, 112 reviews

Little House Inn

NO CLEANING FEES - NO CHORE LIST Reconnect with loved ones in this family-friendly place. Our little house is situated on an acre and a half of land surrounded by wetlands and woods yet minutes from local colleges and amenities. Enjoy the beautiful night sky while relaxing by the fire pit. Or enjoy the woodland view from your deck with your morning coffee. Deer, turkeys, bunnies, and many native birds are regular visitors. Check out our guidebook for places to eat & things to do.

Mar. 19 – 26

$212 CAD per night

Guest favourite

Home in Preston

4.96 out of 5 average rating, 601 reviews

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Oct. 25 – Nov. 1

$300 CAD per night

Guest favourite

Home in Feeding Hills

4.89 out of 5 average rating, 884 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, good for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Sep. 8 – 15

$181 CAD per night

Guest favourite

Home in Bristol

4.93 out of 5 average rating, 115 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Nov. 8 – 15

$235 CAD per night

Guest favourite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

Jun. 9 – 16

$262 CAD per night

Guest favourite

Home in Manchester

4.94 out of 5 average rating, 176 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.

Sep. 26 – Oct. 3

$166 CAD per night

Guest favourite

Home in Southwick

4.99 out of 5 average rating, 181 reviews

Linny's Lakeview Cottage

Linny's lakeview cottage is updated with beautiful hardwood floors. The kitchen is finished in white shaker cabinets, granite counter tops & new ss appliances. The counter joins the kitchen/living room & comfortably sits 6. This is a renovated 650 sq ft home. Access our online guidebook (a few day before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay.

Dec. 9 – 16

$230 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Simsbury house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

Apr. 15 – 22

$232 CAD per night

Guest favourite

Home in Litchfield

4.93 out of 5 average rating, 163 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Sep. 12 – 19

$1,183 CAD per night

Guest favourite

Home in Montville

4.96 out of 5 average rating, 106 reviews

Casino Stay & Play House

May 16 – 23

$706 CAD per night

Superhost

Home in New London

4.89 out of 5 average rating, 131 reviews

OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS

Jul. 31 – Aug. 7

$1,090 CAD per night

Guest favourite

Home in North Salem

4.99 out of 5 average rating, 220 reviews

Converted Barn House

Sep. 20 – 27

$408 CAD per night

Guest favourite

Home in New Hartford

4.91 out of 5 average rating, 11 reviews

Mountain Serenity Lake View Pool & Hot Tub

Apr. 9 – 16

$1,010 CAD per night

Guest favourite

Home in Middletown

4.95 out of 5 average rating, 19 reviews

Hot Tub and pool Home away from home

Jun. 2 – 9

$506 CAD per night

Guest favourite

Home in Litchfield

4.94 out of 5 average rating, 33 reviews

Woodland Country Retreat w/ Pool Near Wineries

Sep. 29 – Oct. 6

$878 CAD per night

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Weekly house rentals

Guest favourite

Home in Granby

4.84 out of 5 average rating, 158 reviews

Clean, Spacious 3 BR Half-Duplex on Quiet 4+ Acres

Aug. 10 – 17

$238 CAD per night

Guest favourite

Home in Great Barrington

4.96 out of 5 average rating, 213 reviews

Jaw dropping mountain & lake views

Nov. 18 – 25

$1,184 CAD per night

Guest favourite

Home in Lyme

4.97 out of 5 average rating, 189 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

May 9 – 16

$488 CAD per night

Guest favourite

Home in Washington

4.85 out of 5 average rating, 170 reviews

Country Home on a Hill

Dec. 27 – Jan. 3

$238 CAD per night

Guest favourite

Home in Coventry

5.0 out of 5 average rating, 105 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

Jan. 20 – 27

$363 CAD per night

Guest favourite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Apr. 8 – 15

$266 CAD per night

Guest favourite

Home in Simsbury

4.98 out of 5 average rating, 88 reviews

Nature House, water view, gazebo. 2 large decks

Nov. 14 – 21

$323 CAD per night

Guest favourite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

Nov. 29 – Dec. 6

$426 CAD per night

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Private house rentals

Guest favourite

Home in New Hartford

4.97 out of 5 average rating, 29 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

Oct. 10 – 17

$368 CAD per night

Guest favourite

Home in Bloomfield

4.94 out of 5 average rating, 88 reviews

Spacious Charming New England Cape

Apr. 19 – 26

$711 CAD per night

Guest favourite

Home in Canton

4.99 out of 5 average rating, 84 reviews

Best River View, on Rail Trail in Collinsville!

Jan. 27 – Feb. 3

$505 CAD per night

Guest favourite

Home in West Hartford

5.0 out of 5 average rating, 17 reviews

The little house that could!

Mar. 21 – 28

$236 CAD per night

Guest favourite

Home in Farmington

5.0 out of 5 average rating, 41 reviews

Lake Escape: New Lake Cottage Charm, AC

Jan. 25 – Feb. 1

$620 CAD per night

Guest favourite

Home in Springfield

5.0 out of 5 average rating, 9 reviews

Quiet 2 Bedroom - near Big E, Massmutual, Six Flag

Nov. 30 – Dec. 7

$224 CAD per night

Guest favourite

Home in Haddam

5.0 out of 5 average rating, 78 reviews

Cozy Comforts!

Aug. 18 – 25

$226 CAD per night

Guest favourite

Home in West Hartford

4.97 out of 5 average rating, 36 reviews

Sprawling Classic New England Home

Aug. 6 – 13

$763 CAD per night

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Quick stats about house rentals in Simsbury

Total rentals
20 properties
Local attractions
Abigail's Grille and Wine Bar, Flamig Farm, and Simsbury Commons
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
1K reviews

House vacation rentals in Simsbury

Top-rated house rentals in Simsbury

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simsbury house rentals

House rentals with a pool

Home in Cheshire

Home in Litchfield

Home in Montville

Home in New London

Home in North Salem

Home in New Hartford

Home in Middletown

Home in Litchfield

Weekly house rentals

Home in Granby

Home in Great Barrington

Home in Lyme

Home in Washington

Home in Coventry

Home in Danbury

Home in Simsbury

Home in Simsbury

Private house rentals

Home in New Hartford

Home in Bloomfield

Home in Canton

Home in West Hartford

Home in Farmington

Home in Springfield

Home in Haddam

Home in West Hartford

Quick stats about house rentals in Simsbury

Total rentals

Local attractions

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Total number of reviews

Destinations to explore