Holiday rentals in Simsbury

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Top-rated holiday rentals in Simsbury

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Top guest favourite

Cottage in Burlington

4.98 out of 5 average rating, 118 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

Guest favourite

Flat in West Granby

4.9 out of 5 average rating, 131 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Welcome to the most beautiful area of CT! 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.

Guest favourite

Cabin in Bloomfield

4.98 out of 5 average rating, 126 reviews

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary

Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

Top guest favourite

Home in Granby

4.95 out of 5 average rating, 250 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 game room 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 .

Top guest favourite

Home in Bloomfield

4.96 out of 5 average rating, 125 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails in winter too! Close to Skiing, MGM Casino, tons of golf courses, beaches. Need a few more rooms? Ask about our 3br house next door which may be available.

Guest favourite

Cottage in Collinsville

4.97 out of 5 average rating, 139 reviews

The Carriage House

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Top guest favourite

Barn in Bloomfield

4.98 out of 5 average rating, 121 reviews

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Top guest favourite

Home in Collinsville

4.99 out of 5 average rating, 114 reviews

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!

Top guest favourite

Guest suite in Bloomfield

4.99 out of 5 average rating, 115 reviews

Guest Suite with Private Entrance & View

Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Guest favourite

Guest suite in East Granby

4.85 out of 5 average rating, 357 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Top guest favourite

Guest house in Granby

4.99 out of 5 average rating, 821 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest favourite

Cottage in Granby

4.89 out of 5 average rating, 198 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

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Other great holiday rentals in Simsbury

Guest favourite

Flat in Collinsville

4.92 out of 5 average rating, 37 reviews

Cozy river-view apartment

MimiRating, 5 stars2 weeks ago

This location was perfect for us—five minutes from family and by the scenic Farmington River. Tammy provided a nice welcome note, snacks and clear instructions. Only suggestion would be to touch up the bathroom paint.

Top guest favourite

Home in Windsor

4.98 out of 5 average rating, 55 reviews

Relax By The Water

Meera (& Eliot!)Rating, 5 stars3 weeks ago

Bryan and June’s place is peaceful and cozy, and the location by the river is spectacular. The kitchen was really comfortable, clean and usable with lots of cookware and nice quality dishes to eat off of; we easefully made multiple meals together and really enjoyed doing it - which isn’t always the case with Airbnbs. Both bedrooms are lovely, so if you’re in a group that needs both bedrooms, this is a rare find where EVERYONE gets “the nice room.” A rare find!! The beds are comfy and on the softer side, and should work great for 99% of people (they were just fine for my spouse and for our friend who traveled with us). IF you are someone who needs an especially firm and supportive bed due to back issues (my situation, sigh), they may not work for you. I’m only sharing that for anyone else in my very specific position, since I also rely on reviews for info like this!

Top guest favourite

Guest suite in Bloomfield

4.94 out of 5 average rating, 100 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

ChrisRating, 5 stars5 days ago

We were in town for a soccer game and this was the perfect place for us to stay, our dogs loved it too!

Guest favourite

Flat in Simsbury

4.9 out of 5 average rating, 20 reviews

Newly Renovated Apartment

BrendaRating, 5 stars1 week ago

We stay here each time we come to Connecticut. It is so neat and clean and has everything you need in it. It is close enough to our son’s place and all the things we want to do. He has been so helpful whenever we have a question we highly recommend staying here.

Guest favourite

Flat in Bloomfield

5 out of 5 average rating, 16 reviews

Bloomfield Bungalow

DeannaRating, 5 stars5 days ago

We had a great stay! The location was perfect—quiet, peaceful, and close to everything we needed. Decor was beautiful. We did encounter a few minor issues during our stay, but Anthony was extremely respectful and responsive, quickly addressing everything we brought up. Check-in and check-out were smooth and very convenient. Overall, it was a very comfortable experience and we’d definitely want to stay again.

Top guest favourite

Guest suite in Farmington

5 out of 5 average rating, 43 reviews

The Cottage at Apple Hill

JanetRating, 5 stars6 months ago

Oh my gosh, I loved this Airbnb! Not only is it charming, cozy and clean, it is aesthetically beautiful inside and out. The property is absolutely gorgeous and they have done such a good job. The house is old and almost on the historic level, but the design and functionality of the Airbnb does not feel dated at all. It’s attached to the main house, but I didn’t hear a thing! Karen was the most responsive host ever and gave me a little tour when I arrived. She truly cares about the guest experience. The only thing to note is that if you are over 6’1” the upstairs bedroom and bathroom might be a bit tight for you. It was perfect for me, but I could see a super tall person having trouble with the short ceilings.

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