Cottage holiday rentals in Tolland County

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Tolland County

Cottage rentals with a hot tub

Guest favourite
Cottage in Guilford
4.95 out of 5 average rating, 181 reviews

Luxury cottage by the sea with hot tub and pool

LauraRating, 5 stars2 weeks ago
My friend and I stayed here for a quick two-night getaway and had a great experience. The space is quiet, cozy, and super well taken care of. The view of the water from the living area is beautiful, and we spent both mornings sitting outside with coffee, and afternoons enjoying the view from the hot tub. We appreciated that the kitchen was fully stocked with all the cooking equipment we needed for nights in—and that Mary had a whole list of spots to check out for adventures out (local shops, antique spots, and really solid lobster rolls!) If you’re looking for a low-key, clean, calm place to relax, recharge, and still have easy access to town, this is a great pick. We’d absolutely come back.
Superhost
Cottage in Litchfield
4.86 out of 5 average rating, 346 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

LisaRating, 5 stars5 days ago
My boyfriend and I had a nice and relaxing one night stay at Martin’s place. It’s a cute house and we enjoyed relaxing in the hot tub! Martin was responsive and communicative. Overall a nice little getaway.
Top guest favourite
Cottage in Plymouth
5 out of 5 average rating, 20 reviews

Lakefront Escape | Cool Tub | Game Room | Fire Pit

RamonRating, 5 stars4 days ago
Such a lovely home! actually better than I expected! Will definitely book again. It’s honestly a no brainer after staying there. I can recommend this place 100%!
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars5 days ago
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.
Guest favourite
Cottage in Woodstock
4.86 out of 5 average rating, 63 reviews

Lakefront Cottage Complete with Kayaks!

PauletteRating, 5 stars2 weeks ago
Absolutely loved the house on the lake. So well appointed, super clean, kitchen was totally equipped and the surrounding was beautiful and quiet. We highly recommend!
Cottage in Monterey
4.68 out of 5 average rating, 19 reviews

mountain refuge

JoshuaRating, 5 stars4 months ago
My girlfriend and I had a great time staying at Joktan’s place. We really enjoyed the home as well as the amenities that came with it. Joktan, provided excellent communication. Would recommend staying here!
Guest favourite
Cottage in Ledyard
4.93 out of 5 average rating, 254 reviews

Lakeside cottage with beautiful views up the lake!

KerriRating, 5 stars3 weeks ago
We always love going to this cottage. It’s our favorite. It’s actually one of our favorite places. To go a few times a year winter summer. We just spent memorial weekend there. A little doggies loved it. Home away from home so cozy. Bobby the host is wonderful. My daughter boyfriend came up and they absolutely loved it and my son came from Texas to spend one night. It was his first time there he loved it. We already planning on going back. Fantastic getaway. If you need to distress and want calmness. This is the place to come to. And the town of Mystic has great restaurants Like I said it’s our favorite place to come to and I’ve been to quite a few…. Just got home today and I’m seeing if I can book some sometime in October to go back we love it.
Cottage in Old Lyme
4.82 out of 5 average rating, 224 reviews

Private Beach Cottage

GraceRating, 5 stars3 weeks ago
Great communication with host, beach within walking distance was so nice, overall good spot within 30 mins of mystic aquarium and Foxwoods casino

Pet-friendly cottage rentals

Guest favourite
Cottage in Middlefield
4.92 out of 5 average rating, 247 reviews

Lake Beseck cottage

MaryRating, 5 stars3 weeks ago
We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!
Guest favourite
Cottage in Becket
4.95 out of 5 average rating, 274 reviews

Berkshires Cottage by Lake. Year Round Adventures.

MichaelRating, 5 stars2 months ago
Had a great stay at Scott’s cottage. Felt right at home It was very comfortable and clean.
Guest favourite
Cottage in Charlestown
4.9 out of 5 average rating, 174 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

JoshuaRating, 5 stars1 week ago
The house was very nice and comfortable for 5 adults, a child, and 2 dogs. Being able to walk down the stairs from the deck and literally be on the beach was incredible. Fantastic space, gorgeous views, and luckily the perfect weather to enjoy it all! Can't wait to rent again next year!
Top guest favourite
Cottage in Groton
4.96 out of 5 average rating, 318 reviews

Charming Historic Schoolhouse on Mystic River

KarenRating, 5 stars5 days ago
We had such a fantastic stay at this special home right on the river in lovely Mystic! It came stocked with everything we needed for a fun couple’s getaway. Gerard was so friendly and accommodating - we felt right at home. Can’t wait to return!
Top guest favourite
Cottage in Ledyard
4.91 out of 5 average rating, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

OliviaRating, 5 stars1 month ago
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!
Top guest favourite
Cottage in Guilford
4.94 out of 5 average rating, 269 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars2 weeks ago
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 273 reviews

Charm + location. Walk to beach, town, & harbor.

MaryRating, 5 stars2 weeks ago
Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.
Guest favourite
Cottage in Milford
4.95 out of 5 average rating, 325 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

LeaRating, 5 stars1 day ago
This house was perfect for my anniversary getaway. It was a short 4/5 min walk to the beach. The house itself was great. The neighborhood was super peaceful and the surrounding restaurants were good as well. Definitely would make this a yearly visit. Thank you so much for the amazing stay

Private cottage rentals

Top guest favourite
Cottage in East Haddam
5 out of 5 average rating, 15 reviews

New & Beautiful Lake cottage

SharonRating, 5 stars3 weeks ago
The cottage is on a beautiful lake and is very relaxing . The morning sunset on our second day was amazing. Perfect couples retreat or in our case girls weekend. Our host, Donna, was very responsive and provided extra goodies. The house was clean and comfortable. We visited Gillette’s Castle and downtown Chester had lunch at Market 37 . Unfortunately, we had rain and could not enjoy deck right on the water.
Guest favourite
Cottage in Dudley
4.84 out of 5 average rating, 43 reviews

Cozy, 3BR lake-side retreat and outdoor oasis

GraceRating, 5 stars3 months ago
Was a great stay for my family and I.
Guest favourite
Cottage in East Haddam
5 out of 5 average rating, 14 reviews

Cozy Lakefront Cottage Perfect for Families

CassidyRating, 5 stars3 weeks ago
What a beautiful view! We had a great time despite the weather. The house was very comfortable and the location right on the lake is hard to beat.
Top guest favourite
Cottage in Killingly
4.88 out of 5 average rating, 76 reviews

Lake front Cottage located on Alexander’s Lake

PaulRating, 5 stars3 weeks ago
Such a beautiful place to stay! Alexander’s Lake is gorgeous and this lovely cottage sits right on the water allowing you to take the kayaks out to explore the lake. I even got lucky while fishing from the dock and the kayak! Great views in the morning and evening. Very quiet neighborhood. Will definitely be looking to stay again!
Guest favourite
Cottage in Lebanon
4.98 out of 5 average rating, 40 reviews

"The Napping House". Lake front, kayaks, fire pit.

KristinaRating, 5 stars1 week ago
We LOVED our stay at Scott's place! I felt all my stress melt away as soon as I arrived. Withing ten minutes I was swimming in the lake! I had a blast kayaking. We had some storms one night, but were still able to spend a lovely evening on the porch watching the skies - which did break in time for a beautiful sunset! My point in telling that is that Scott's place is set up for enjoyment no matter the weather. The home was very comfortable, and it is now on my list to make regular get-aways.
Top guest favourite
Cottage in Brimfield
4.99 out of 5 average rating, 70 reviews

Cheerful 2 bedroom cottage with lake access.

KathleenRating, 5 stars2 weeks ago
This was the perfect spot for our mini vacation with our adult son and dog. The house was adorable and comfortable...the beds were especially comfy. The fenced in patio area and sun porch was so relaxing and although no one actually slept on it, the daybed was very comfortable as well. We enjoyed our day trip to Boston and multiple trips to Treehouse Brewery. Gwen's communication was awesome...such a terrific host! Hoping to stay again.
Guest favourite
Cottage in Seymour
4.93 out of 5 average rating, 56 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

JamieRating, 5 stars1 week ago
My family and myself loved every square inch of this property! From the serene views and well landscaped garden, to the sound of a stream to fall asleep to, the spotless interior and attention to detail…the pet bowls and bed, the labeled cabinets, the toiletries and games, we never wanted to leave! We last minute had to accommodate family members to be picked up later than the check out time and Michael was kind enough to extend our stay until 2pm so we could relax and enjoy more time together! We might make an annual trip out of this house and can’t thank the host enough for his immediate responses and making us feel right at home. Beautiful home, we loved sharing it! The first night we ate at the near by restaurant on the water, Housatonic House, also a recommendation on the fridge! Great food and service and BEAUTIFUL views! It ended up raining Saturday, but we still got a Hike in on our last morning at Osbornedale State Park, beautiful trails and picnic areas! Wonderful time.
Top guest favourite
Cottage in Old Lyme
4.98 out of 5 average rating, 55 reviews

Studio Four-Entire Guesthouse near CT River

JoshuaRating, 5 stars3 weeks ago
Very private nicely appointed and great hosts

Destinations to explore