Holiday houses in Sherman

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Top-rated holiday rentals in Sherman

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

Guest favourite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 79 reviews

Apartment in Lovely Lake House,Pets welcome!

ChrisRating, 5 stars1 month ago
We could not say enough about this place! It was fully equipped with everything you could think of and more. Bee let us check in early and was extremely helpful answering any questions we had a long the way. We will most definitely be back on our next trip home. This air b n b sets the bar for all other air b n b’s from here on out. The price range felt as though it should’ve been more for this top notch experience. 12/10 would recommend! Thank you for being so attentive, understanding with our noisy, anxious dog (our apologies again!) and fast responsive communication! Until next time Greenwood Lake!
Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 115 reviews

Time to escape to the lake!Hot-tub/1 hour from NYC

ChristineRating, 5 stars3 weeks ago
The house is exceptional inside and out. The house was clean and cozy, and the surroundings were scenic with a beautiful view of the lake right outside and from the living room window. Made for a fun, peaceful and relaxing stay!
Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Family I Fire Pit I Kayaks

JulietteRating, 5 stars3 months ago
We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!
Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 48 reviews

Explore a Luxurious Lakefront Dream Home

AndrewRating, 5 stars3 weeks ago
Wonderful place for getaway . Beautiful home and the host was extremely helpful.
Guest favourite

Home in Great Barrington

4.95 out of 5 average rating, 20 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

SarahRating, 5 stars7 months ago
The house is set back from the road in an inviting tree lined yard and felt “tucked in”. Loved the house book with detailed instructions. The hot tub was pretty easy to use - just a few missteps on our part. Every level had great amenities. All three beds we used were extraordinarily comfortable. Bathrooms extraordinarily clean!!
Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 462 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

AugustRating, 5 stars2 days ago
This cabin is very cool. Rustic and comfortable, and a five minute drive in any direction from a number of great restaurants and things to do. The sauna was so lovely, the whole place felt like you had the joy of cabin living without actually having to rough it, if that makes sense. Jon was very responsive, had a ton of recommendations in the area, and when we had a question, he was, and please excuse this terrible but necessary joke, Johnny-on-the-spot. If we liked hiking, there were places to do that very near. We don’t, so we didn’t do any of that - but other people should! All in all, great stay, great experience, very relaxing. 10 of 10, would recommend.
Superhost

Chalet in Goshen

4.89 out of 5 average rating, 134 reviews

The Goshen Glass Chalet

WilfredoRating, 5 stars2 weeks ago
a beautiful stay for sure, very peaceful and removed from the city. My girlfriend and I will be staying there again for sure
Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

StefanieRating, 5 stars2 months ago
A quick weekend girls trip. We enjoyed the outside space, porch, corn hole and view. Beds and couch were comfy. Would stay again!
Guest favourite

Townhouse in Hunter

4.91 out of 5 average rating, 70 reviews

Stunning Mountain View Catskill Vacation Escape

MelissaRating, 5 stars1 month ago
Wow! This listing does not do this place justice. I've never taken this type of vacation before. I am a beach go-er, but I brought my son snowboarding for his birthday. The townhouse was absolutely perfect. It was spacious, clean, and comfortable, and so close to the mountain. There were so many thoughtful amenities throughout. I especially appreciated the explicit driving directions as I am directionally challenged! haha. My boys are already talking about a return trip to Hunter Mountain. As beautiful as the hotel was, I can't imagine being as comfortable as we were here. This will be the first place I look for availability on our next trip.
Guest favourite

Home in Putnam Valley

4.96 out of 5 average rating, 54 reviews

Waterfront Lake House

VictoriaRating, 5 stars1 month ago
Amazing place, beautiful views! Great host!
Guest favourite

Condo in Hunter

4.89 out of 5 average rating, 84 reviews

Cozy Slope Side Retreat

MichaelRating, 5 stars1 week ago
We had a awesome ski vacation at Hunt. Easy walk to the slopes and back. Fantastic location- nicely away from the crowds of the main lodge area, but walking accessible to the slopes.
Guest favourite

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

MusaRating, 5 stars1 month ago
Lovely place great location near short beach and an easy walk to a great Italian restaurant

Popular amenities for Sherman holiday rentals

Stay near Sherman's top sights

American Pie Company34 locals recommend
White Silo Farm & Winery30 locals recommend
Squantz Pond State Park30 locals recommend
Bulls Covered Bridge27 locals recommend
Sherman Wine & Liquor16 locals recommend
Sherman Players12 locals recommend

Other great holiday rentals in Sherman

Guest favourite

Home in Millerton

4.96 out of 5 average rating, 168 reviews

Vacation Home In Millerton

MikeRating, 5 stars1 week ago
Great house in the woods. Had everything we needed. Will look to rent again next year for our yearly hockey tournament.
Guest favourite

Chalet in Hunter

4.98 out of 5 average rating, 144 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

RhiannaRating, 5 stars4 weeks ago
Nataliya's place was beautiful and a great getaway while skiing at Hunter Mountain. Would recommend for any big group or family.
Guest favourite

Home in Tannersville

4.97 out of 5 average rating, 74 reviews

CottageintheClouds-InVillage 3BR 2BA, King bed

JeffreyRating, 5 stars1 week ago
We came for a weekend skiing at Hunter and Donna's place was perfect... Location in the town of Tannersville was great, we could walk down to the restaurants/shops in town. Less than a 10 minute drive to the slopes at Hunter. Everything in the home was as described and just what we needed - from the kitchen to the bedrooms to the living space. And Donna was super flexible and responsive as we had a few questions leading up to our stay.
Superhost

Home in Putnam Valley

4.73 out of 5 average rating, 37 reviews

The Blue Lake House!

Kevin Rating, 5 stars2 months ago
Paula's home was the perfect weekend getaway for my family, and the only thing better than the location was the weather. We were able to enjoy the beautiful lakefront and walk around the neighborhood as well as enjoy all the sights to see in the neighboring town. The house was spacious enough to relax while also having fun and making new memories. We would love to stay here again in the future!
Guest favourite

Cottage in Greenwood Lake

4.96 out of 5 average rating, 46 reviews

5 bedroom 7 beds Cottage Relax, Hike, Winery & Ski

PamRating, 5 stars1 month ago
Very communicative! We had small problem and they were very responsive! The house is so cute. We were here during winter which was beautiful but would imagine this place would be beautiful anytime of year
Guest favourite

Cabin in Shandaken

4.99 out of 5 average rating, 103 reviews

A Place Called Home in The Catskill

AliciaRating, 5 stars4 weeks ago
We really enjoyed our stay. We had three families and the space accommodated us well. John’s place is well located to Bellayre - 15 min away. The kitchen and layout were great and the house is very comfortable. I definitely recommend it and would stay again. Thanks for a great stay!!
Guest favourite

Home in Tannersville

4.92 out of 5 average rating, 26 reviews

Beautiful Home in the Woods - Hot Tub - Ski Nearby

RebeccaRating, 5 stars1 week ago
The house is amazing! It is even more gorgeous than the pictures. And Svetlana was an amazing host. Super communicative and answered all our questions and more. 10/10 stay
Guest favourite

Home in Milford

5 out of 5 average rating, 6 reviews

Big House On Maddox

DianeRating, 5 stars4 months ago
We stayed here in the entire home for a wedding weekend. Both units were fabulous and Cole was very responsive when we had an issue with the key pad. The bride

Quick stats about holiday rentals in Sherman

  • Total rentals

    50 properties

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Sherman