House holiday rentals in Simsbury

4.95 out of 5 average rating, 123 reviews

The exterior of a newly renovated schoolhouse is depicted, showcasing a welcoming entrance with a red door. Surrounding greenery includes well-maintained lawns and established trees. A carriage house is visible on the left, complementing the charming architecture of the main house.

Home in Collinsville

Nature Lovers Retreat-Wine Vineyards nearby

Sleeps 6! Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP , canoeing kayak rentals

ValueLocationCheck-in

4.99 out of 5 average rating, 248 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

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.

LocationValueHot tub

4.99 out of 5 average rating, 183 reviews

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a BEAUTIFUL WATERFRONT, 3 bedrooms/3 full bathrooms and a year-round outdoor JACUZZI Also included: gorgeous primary bedroom suite, artistic furnishings, cozy FIREPLACE, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, KAYAKS, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

LocationFamilySleep quality

4.98 out of 5 average rating, 116 reviews

An outdoor deck features a large table surrounded by several comfortable chairs. A gas fire pit is centrally located on the table, and a grill is positioned nearby. Lush greenery can be seen in the background, enhancing the outdoor space.

Home in West Hartford

Prime West Hartford Center Location: Historic Gem

With over 500 five star guest reviews, Mark Chu Rentals is known for exceptional hospitality, thoughtful details, and memorable stays. Enjoy the perfect blend of historic charm and modern comfort in the heart of West Hartford Center. Relax on the spacious private deck with a gas fire pit and grill, or take a short walk to Blue Back Square for boutique shopping, restaurants, cafés, and entertainment. The nearby Delamar Hotel makes this an ideal location for business and leisure travelers alike.

ValueFamilyWalkability

4.88 out of 5 average rating, 189 reviews

A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.

Home in South Windsor

Spacious 3 Bedroom Ranch With Office

Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

ValueFamilyHeating

4.93 out of 5 average rating, 345 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

LocationFamilyPool

4.93 out of 5 average rating, 238 reviews

A comfortable sleeping area features a dark tufted headboard and a soft, neatly arranged bedding with multiple pillows. A lamp is positioned on a bedside table, while a floor lamp provides additional light. A floral wall art piece adds a subtle touch above the bed.

Home in Manchester

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

LocationFamilyBathroom

4.95 out of 5 average rating, 116 reviews

A welcoming living room features a comfortable couch and two textured armchairs, arranged around a central round coffee table. Natural light filters through large windows, highlighting a cozy atmosphere. A small side table displays a plant and a soft throw blanket.

Home in New Britain

Bright & Private WHOLE HOUSE 4 YOU Near Everything

Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

ValueLocationLong stay

4.91 out of 5 average rating, 105 reviews

A spacious living area features high ceilings with exposed beams and wooden flooring. Comfortable seating includes sofas and chairs arranged around a central coffee table. A large television is set against one wall, and plants add a touch of greenery to the room.

Home in Windsor

Island Vibes

Come and enjoy a tranquil stay with an island vibe. This 3 bedroom, 2 bath home will comfortably accommodate up to 8 persons. Large kitchen and living space for everyone. Situated in a quiet suburb on the outskirts of downtown Hartford, it is 12 minutes from Bradley International Airport, 20 minutes from the Basketball Hall of Fame and Springfield Museums Quadrangle. In the region is the Connecticut Science Museum, The Mark Twain House, Wadsworth Atheneum Museum of Art, and much more.

LocationFamilyCleanliness

4.99 out of 5 average rating, 138 reviews

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

Home in Canton

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

LocationFamilyWi-Fi

4.89 out of 5 average rating, 158 reviews

A bright living room features a cozy arrangement with a gray sofa and two wooden chairs. A simple coffee table displays decorative items and a potted plant. Natural light streams through two windows, adorned with bamboo shades, creating a warm and inviting space.

Home in New Hartford

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.

FamilyLocationGetting around

4.97 out of 5 average rating, 307 reviews

The exterior of a renovated farmhouse is surrounded by lush greenery and flowering shrubs. A stone pathway leads to the front porch, which features a pair of chairs. A barn is visible in the background, set against a backdrop of trees and hills.

Home in Russell

South Quarter House

Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

LocationFamilyCondition

Popular amenities for Simsbury house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.83 out of 5 average rating, 116 reviews

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

Home in Litchfield

The Getaway-HOST & Co.

ValueLocationComfort

4.93 out of 5 average rating, 212 reviews

A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 45 reviews

Home in East Haddam

15 acres! * Pine Pond at Devils Hopyard State Park

FamilyValueParks

4.98 out of 5 average rating, 86 reviews

The exterior of a two-story waterfront home is shown, featuring a modern design with blue siding. A spacious deck is visible above a landscaped area with carefully arranged plants and gravel, while a driveway leads to the front of the house, surrounded by greenery.

Home in Rocky Hill

Cozy Waterfront Home w/Hot Tub ~ Connecticut River

LocationFamilyNearby

4.97 out of 5 average rating, 32 reviews

The spacious bedroom features a large bed with a navy blue comforter, complemented by two decorative pillows. A dark wooden dresser and two nightstands with lamps are present. Natural light enters through a window and a skylight above. A geometric patterned area rug enhances the floor space.

Home in East Hartford

Family Retreat Near Hartford – Year-Round Getaway

LocationFamilyAccuracy

4.95 out of 5 average rating, 19 reviews

A two-story house features light yellow siding with blue shutters around the windows. The front yard is well-maintained, showcasing green grass and neatly trimmed bushes on either side of the entrance. A concrete driveway runs alongside the home.

Home in Enfield

Enjoy New England weather and comforts of home!

LocationFamilyLong stay

4.96 out of 5 average rating, 85 reviews

The historic two-family home is bordered by lush greenery and blooming flowers. A white picket fence frames the vibrant garden, while the house features dark shutters and a welcoming front porch. A winding pathway leads to the entrance, inviting guests into the serene surroundings.

Home in East Hampton

Country getaway - pool, huge yard,

FamilyLocationPool

4.94 out of 5 average rating, 70 reviews

Home in Wolcott

Amazing Paradise, Seasonal Pool, BBQ, Pool Table.

LocationValueQuiet

Weekly house rentals

4.87 out of 5 average rating, 304 reviews

A fire pit is surrounded by five blue Adirondack chairs on a grassy area, overlooking a calm body of water. Lush green trees create a natural backdrop, and a cloudy sky reflects a tranquil and serene outdoor setting.

Home in Enfield

Scenic River View

LocationValueCheckout

4.85 out of 5 average rating, 131 reviews

A charming red homestead is surrounded by a light coating of snow, with a wooden staircase leading to the entrance. Leafless trees are visible in the foreground, and a convenience store can be seen in the background, enhancing the house's accessibility.

Home in Torrington

Charming Home in Litchfield County on a MAIN ROAD!

LocationFamilyQuiet

4.9 out of 5 average rating, 108 reviews

A spacious living area features a red sectional sofa and a small round coffee table with a plant centerpiece. The open layout connects to a well-lit kitchen in the background, visible through a doorway, blending comfort and functionality.

Home in Manchester

Charming Cape Home, Close to All

FamilyLocationDecor

4.92 out of 5 average rating, 234 reviews

The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

LocationFamilyBackyard

4.84 out of 5 average rating, 119 reviews

A bright living area features a teal sofa paired with a light gray armchair, accented by a round coffee table at the center. Natural light floods in through large windows, with soft curtains enhancing the serene atmosphere. Art pieces adorn the walls, complementing the hardwood floor.

Home in Bristol

Stylish & Luxurious 3 BDR home with Play Station

ValueLocationOutdoor spaces

4.94 out of 5 average rating, 286 reviews

Home in Tolland

The Carriage House

FamilyValueIndoor spaces

4.98 out of 5 average rating, 330 reviews

A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.

Home in Bethlehem

Litchfield County Farmhouse with a Modern Twist

LocationValueSkiing

5.0 out of 5 average rating, 53 reviews

A charming cottage is set against a backdrop of lush greenery. The exterior features light-toned siding, a vibrant red door, and flower boxes with colorful blooms. Steps lead to a welcoming entrance, complemented by landscaped areas of mulch and small shrubs.

Home in Simsbury

Charming Cottage next to Flamig Farm

ValueFamilyBreakfast

Private house rentals

4.99 out of 5 average rating, 160 reviews

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

Cozy Comforts!

FamilyLocationParks

5.0 out of 5 average rating, 11 reviews

Home in Granby

Lake House Retreat Granby CT

FamilyLocationKitchen

4.87 out of 5 average rating, 47 reviews

An outdoor firepit area is surrounded by natural scenery, featuring light-colored chairs and a wooden swing suspended from a pergola. The ground is covered in white gravel, with scattered leaves from nearby trees, creating a peaceful spot for gatherings.

Home in Barkhamsted

Woodland Sanctuary-hot tub|fireplace|hikes|fishing

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 21 reviews

Home in Southwick

The Overlook at Lake Congamond

LocationFamilyCondition

4.99 out of 5 average rating, 80 reviews

A serene sunset over a private lake is captured, showcasing soft pink and orange hues reflected on the smooth water's surface. Silhouettes of trees line the shore, creating a tranquil backdrop to the beauty of the evening sky.

Home in Farmington

Lake Escape: Lake Cottage Charm, Lake Front, AC

LocationFamilyBathroom

4.98 out of 5 average rating, 48 reviews

Home in Windsor Locks

The Hangar

LocationValueHospitality

4.95 out of 5 average rating, 40 reviews

Home in Winchester

Highland Lakefront Retreat

LocationFamilyOutdoor spaces