House vacation rentals in Simsbury

Find and book unique houses on Airbnb

Top-rated house rentals in Simsbury

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

0 of 0 items showing

1 of 3 pages

Guest favorite

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 1 – 8

ﺩ.ﺇ842 per night

Guest favorite

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.

Mar 29 – Apr 5

ﺩ.ﺇ603 per night

Guest favorite

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 .

Aug 31 – Sep 7

ﺩ.ﺇ638 per night

Guest favorite

Home in Granby

4.83 out of 5 average rating, 157 reviews

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

Spacious duplex (1600+ SQ Feet)with full kitchen, washer and dryer in unit, on 4+ acres to enjoy. OTHER DUPLEX IS OWNER OCCUPIED. Home is set back 800+ feet off main road on an old christmas tree farm. TVs in living room and master bedroom with Netflix. Property located off RT 202 for easy travel to surrounding towns, colleges, hiking trails, and various attractions. No parties. Feel free to contact us with any questions! You will see our pup Gronk, as he spends much of his time in the yard.

Sep 10 – 17

ﺩ.ﺇ567 per night

Guest favorite

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.

Mar 9 – 16

ﺩ.ﺇ1,860 per night

Guest favorite

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

ﺩ.ﺇ444 per night

Guest favorite

Home in Bristol

4.93 out of 5 average rating, 114 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.

Apr 4 – 11

ﺩ.ﺇ523 per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 213 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Feb 11 – 18

ﺩ.ﺇ2,690 per night

Guest favorite

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 7 – 14

ﺩ.ﺇ547 per night

Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 227 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Jan 13 – 20

ﺩ.ﺇ842 per night

Guest favorite

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.

Oct 28 – Nov 4

ﺩ.ﺇ363 per night

Guest favorite

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.

Oct 3 – 10

ﺩ.ﺇ636 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 favorite

Home in Litchfield

4.93 out of 5 average rating, 162 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Sep 12 – 19

ﺩ.ﺇ2,692 per night

Superhost

Home in Sheffield

4.85 out of 5 average rating, 114 reviews

Race Mountain House

Jun 23 – 30

ﺩ.ﺇ2,034 per night

Guest favorite

Home in New Hartford

4.91 out of 5 average rating, 11 reviews

Mountain Serenity Lake View Pool & Hot Tub

Mar 18 – 25

ﺩ.ﺇ2,261 per night

Guest favorite

Home in Middletown

4.95 out of 5 average rating, 19 reviews

Hot Tub and pool Home away from home

May 15 – 22

ﺩ.ﺇ1,291 per night

Guest favorite

Home in Morris

4.91 out of 5 average rating, 64 reviews

Luxury Compound, Pool, Gym, Tree House, Game Barn

May 9 – 16

ﺩ.ﺇ1,708 per night

Guest favorite

Home in Litchfield

4.94 out of 5 average rating, 33 reviews

Woodland Country Retreat w/ Pool Near Wineries

Sep 8 – 15

ﺩ.ﺇ1,989 per night

Guest favorite

Home in Goshen

5.0 out of 5 average rating, 46 reviews

Superb Lakefront Getaway with Family and Friends

Feb 9 – 16

ﺩ.ﺇ2,340 per night

Guest favorite

Home in New Marlborough

4.95 out of 5 average rating, 21 reviews

Berkshires Colonial Farmhouse

Dec 11 – 18

ﺩ.ﺇ1,844 per night

Show all

Weekly house rentals

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 189 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

May 9 – 16

ﺩ.ﺇ1,056 per night

Guest favorite

Home in Washington

4.85 out of 5 average rating, 170 reviews

Country Home on a Hill

Apr 17 – 24

ﺩ.ﺇ528 per night

Guest favorite

Home in Coventry

5.0 out of 5 average rating, 105 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

Dec 2 – 9

ﺩ.ﺇ815 per night

Guest favorite

Home in Simsbury

4.98 out of 5 average rating, 88 reviews

Nature House, water view, gazebo. 2 large decks

Nov 14 – 21

ﺩ.ﺇ729 per night

Guest favorite

Home in Simsbury

4.89 out of 5 average rating, 57 reviews

Simsbury Ranch in a quiet neighborhood!

Jan 18 – 25

ﺩ.ﺇ965 per night

Superhost

Home in South Windsor

4.85 out of 5 average rating, 20 reviews

Grampa Potatoes Homestead

Sep 12 – 19

ﺩ.ﺇ475 per night

Guest favorite

Home in Windsor

4.97 out of 5 average rating, 36 reviews

Relax By The Water

Nov 12 – 19

ﺩ.ﺇ747 per night

Guest favorite

Home in West Hartford

4.93 out of 5 average rating, 42 reviews

WeHa Penthouse w/ Private Deck

Aug 9 – 16

ﺩ.ﺇ550 per night

Show all

Private house rentals

Guest favorite

Home in West Hartford

5.0 out of 5 average rating, 17 reviews

The little house that could!

Jul 3 – 10

ﺩ.ﺇ493 per night

Guest favorite

Home in Farmington

5.0 out of 5 average rating, 41 reviews

Lake Escape: New Lake Cottage Charm, AC

Dec 1 – 8

ﺩ.ﺇ1,403 per night

Guest favorite

Home in Springfield

5.0 out of 5 average rating, 9 reviews

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

Jan 30 – Feb 6

ﺩ.ﺇ465 per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 77 reviews

Cozy Comforts!

Dec 30 – Jan 6

ﺩ.ﺇ388 per night

Guest favorite

Home in West Hartford

5.0 out of 5 average rating, 35 reviews

Sprawling Classic New England Home

Dec 8 – 15

ﺩ.ﺇ1,507 per night

Guest favorite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

Dec 16 – 23

ﺩ.ﺇ339 per night

Guest favorite

Home in Agawam

4.99 out of 5 average rating, 88 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Apr 15 – 22

ﺩ.ﺇ898 per night

Guest favorite

Home in Windsor

4.86 out of 5 average rating, 21 reviews

Quiet 3 BRS home with garages

Feb 6 – 13

ﺩ.ﺇ457 per night

Show all

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 Litchfield

Home in Sheffield

Home in New Hartford

Home in Middletown

Home in Morris

Home in Litchfield

Home in Goshen

Home in New Marlborough

Weekly house rentals

Home in Lyme

Home in Washington

Home in Coventry

Home in Simsbury

Home in Simsbury

Home in South Windsor

Home in Windsor

Home in West Hartford

Private house rentals

Home in West Hartford

Home in Farmington

Home in Springfield

Home in Haddam

Home in West Hartford

Home in Becket

Home in Agawam

Home in Windsor

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