Photo by Patricia Mari

Holiday Rentals in Sherman

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Holiday Rentals in Sherman

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (15)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent

Spacious New 5-bedroom holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (6)
"The home was even more stunning in person and from the moment we pulled onto the block we were welcomed by its beautiful surroundings. The home was very comfortable, plenty of space and each of us were very impressed by the thoughtful layout and features. We were in town for a very special event commemorating our brothers amazing achievements and had everything we needed for a very pleasant and memorable stay. The screened in porch was an added bonus and of course, we all gravitated around the...
The price is €718
includes taxes & fees
30 Dec - 31 Dec
Spacious New 5-bedroom holiday house in lovely Hudson Valley

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is €819
includes taxes & fees
2 Dec - 3 Dec
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Peaceful apartment on 3.5 acres w/ artist studio.

9.8 out of 10, Exceptional, (14)
"We were only here for one night on a whirlwind trip but would gladly have stayed a little longer. Cozy, woodsy and comfy. Nice place to relax and recharge! We really appreciated the excellent (real) coffee! No pods here :) Saleem was great - very helpful!"
The price is €204
includes taxes & fees
11 Dec - 12 Dec
Peaceful apartment on 3.5 acres w/ artist studio.

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (26)
"The view in the fall was amazing! So relaxing to sit and watch the lake while having our coffee. The owners are amazing. Everything we needed and more. Plenty of room for the family or even if multiple families stayed. Would stay here again!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay. Property was clean and perfect. Hosts were fantastic. Would return. "
The price is €469
includes taxes & fees
3 Dec - 4 Dec
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (19)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (28)
"Property and home are beautiful. The larger home on adjacent property (Sunny Day) is close and if a larger group is staying there can be loud in the tranquil setting during the day. Otherwise, the setting is beautiful and the house was perfect for our family of 6 (3 couples). We enjoyed the kayak, paddle board, fishing, evening fire pit and views from upstairs deck and downstairs patio. "
Stay 3 Nights or Longer Until January 31 and Get 15% Off

Candlewood Lake Retreat with year round views

10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

9.2 out of 10, Wonderful, (35)
"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (105)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (10)
"Property worked very well for us. Pool was great. (Couple of notes: The stay listed above is slightly incorrect. We arrived on Wed Jun 26 and left on Sun June 30). We requested additional chairs for the pool area from the owner but they were never delivered."
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Traveling Nurse or Business Professional

10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Sherman you may be interested in

Ethan Allen Hotel

3.5 star property
7.8 out of 10, Good, (1119)
"Staff was accommodating with my request for a room on a quiet side. Room was advertised as a suite but was very small with extremely outdated furniture and TV. Very convenient to the Danbury Mall. Ongoing construction outside and inside. Difficult connecting with the desk via phone but they did respond to emails."
The price is €130
includes taxes & fees
8 Dec - 9 Dec
Ethan Allen Hotel

Hotel Zero Degrees Danbury

4.0 star property
9.0 out of 10, Wonderful, (1072)
"I feel cleaning crew could start later, check out isn’t until 11, why start any earlier? Way too much noise in the hallways. "
The price is €176
includes taxes & fees
22 Dec - 23 Dec
Hotel Zero Degrees Danbury

Wyndham Southbury

3.0 star property
8.0 out of 10, Very good, (1140)
"Aimee at the front desk was wonderful and accommodating "
The price is €100
includes taxes & fees
25 Dec - 26 Dec
Wyndham Southbury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Sherman?

Yes, there are holiday rentals close to the most popular sights in Sherman, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Sherman has to offer?

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock: This holiday home rental outside of Sherman is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Sherman?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Sherman stay.

What’s there to see and do in Sherman?

Candlewood Lake and Housatonic River are a couple of lovely local spots to get outside and enjoy nature. Squantz Pond State Park and Elephant's Trunk Flea Market are a couple of places you'll find in the wider area.

What’s a holiday rental in Sherman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sherman. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.