
Winchester fishing vacation rentals
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Top-rated vacation rentals in Winchester
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Lake side house rentals in Winchester

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home
I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

Lakefront, view of ski mtn, firepit, kayaks, dock
The house and view are just as they seem. We had terrible weather the weekend we stayed so we can’t wait to come back and take the kayaks out and enjoy more than just the lake view. But the tranquility was wonderful even in the rain! Extremely convenient to route 2, which was perfect for keeping us busy. We will be back!

Newer Home on quiet 200 acre lake - sleeps 6
This home is beautiful ,well equipped, and the perfect spot to relax. Melora was very friendly and helpful. The little extra touches was what made the home feel so comfortable and the view is just perfect. We are definitely planning a second stay in the near future.

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs
We LOVED our stay here! The lake is so peaceful and the house has the perfect view. Andrew was very helpful and accommodating and we would highly recommend staying here!

Private Lake Front Home
Cozy place with a beautiful view. Had everything we needed and was comfortable to stay with a little baby. Looked even better than the photos. It was super cute!

Lovers Honey Pond Treehouse with hot tub & sauna
Ben's place is special, relaxing and unique. Well thought out details to the cabin, even little things that give it charm. Great communicative and friendly host.

VT Lake House living with sunset views!
Wonderful stay at this lovely lake house. It was exactly as advertised and everything we had hoped it would be. Clean and functional interior and fun lake “toys” provided to make any trip well worth every penny. Thank you for sharing this lake retreat with us! Madison
Winchester fishing house rentals

Wachusett Mountain Get-Away
House was very nice and was perfect for us. Location was convenient to the activities we were attending. Thank you!

Willow Falls Home ~Hot tub & Waterfront
Such an amazing place to stay - easy to get to surrounding towns and local attractions but the physical location and the space lends itself to such a beautiful tranquility and peace we could feel ourselves relaxing the minute we got out of the car. Everything we could have wanted was provided, including a washer and dryer, the beds were so very comfortable, and being able to soak in the hot tub beneath the stars after a long day was just an added bonus. We were so grateful to be able to be in this space for about a week and hope to be able to rerun in the future!

Moonstone Lake House – romantic, serene, fun!
Mighty is fantastic! Her place is brimming with art and comfort, soft colorful rugs, creativity and spirit in every nook and cranny. So many thoughtful details from the toilet seat warmer to the lavender sachets. Just everything. But that lake that meets the back deck. It is magical. What a place and what a kind and caring host.

@SunapeeSeasons—Across from Dewey Beach, Lake View
We really enjoyed our stay at Christopher’s place. It is clean, spacious, and the views are stunning, just a short walk to Dewey beach and Sunapee town. Highly recommend! Perhaps the only (minor) downside was that the place was short on household supplies and there were no grocery stores within a walking distance.

The River House
Would love to come back some day, great trip

Private Waterfront! Views, Hot Tub, King Bed
Great getaway spot for a spring trip with the family! Enjoyed exploring the pond, relaxing in the hot tub and spending quality time in this beautiful home.

Four Season Cozy Cottage on Lake Mattawa
We had a fantastic long weekend on Lake Mattawa. Came to celebrate our son’s graduation from UMass. It was an easy 30 minute drive to campus for graduation. The cottage was a perfect place to hang out as a family…we paddled, fished, played games and cooked. Enjoyed eating on the deck and loved having our morning coffee on the sun porch. Really liked the Quabbin Harvest Coop (awesome local produce and supplies) and had an amazing sandwich at the Corner Cafe. Hope to return!

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.
Other great vacation rentals in Winchester

Cozy Log Cabin Mountain Views
We had a lovely, relaxing stay at Lydia's place. The cottage is roomy, clean, and she kindly gives the option of using the pellet stove (with detailed instructions) or electric baseboard heating located in individual rooms. The view of the mountains and pond are a treat any time of day and we made use of the fire pit in the evenings. Firewood was available on the premises! We would consider staying here again!

Be Still Meadows at Chase Hill Farm - first floor
Johanna’s beautifully updated farmhouse has warmth, character, and exquisite New England charm. I needed a peaceful respite, and this farm was perfect as was Johanna’s responsiveness as a host.

Guilford Grove Cottage
We truly loved staying in this beautiful, cozy cabin. It was just the right size for the two of us, and very comfortable. The view of trees and wildflowers was lovely and refreshing. It was also fun to have a couple of cats walk across the porch each day! Joel was very proactive and friendly, which we greatly appreciated.

The Carriage Barn
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Peaceful forest cottage getaway
We absolutely loved our stay!!! The trail behind the apartment is awesome, and we loved the sound of the brook. We had a turtle friend too! We hope to return!!

Private Dublin apartment nestled in the woods
This beautiful Airbnb is located in a "slice of heaven" with beautiful forested hills surrounding the property. We were hoping for a peaceful location yet close enough to appreciate hikes, coffee shops, restaurants, and venturing into Vermont as well. BINGO! This lovely location for the ticket. Having been on a lengthy road trip, we also were grateful to have laundry facilities and avoid a laundromat. Plus, we were spoiled with homemade bread and cookies awaiting our arrival. Linda was quick to respond to questions plus she and Sterling had a binder filled with many suggestions of things to do in the area. While we hoped to experience the autumn colors on a New England trip, we researched about the beauty and fewer crowds in spring so quickly shifted gears to mid-to-late May!

On the Water at North Bridge Cove
2nd time staying here, lovely little spot on the river. Well-priced and met our needs. Best for 1-2 travelers and folks who either have a car or don't mind the easy walk into town. I'll likely stay here again when I next visit Bratt!

Cottage amongst the trees
John& Aisha’s cottage was the perfect place for our weekend getaway. Conveniently located between Putney and Brattleboro made it easy to get around. The cottage was very clean and well stocked. John and Aisha were super hosts and went above and beyond with local recommendations to activities we could do. Would highly recommend to anyone traveling through VT.
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Manchester Country Club - NH
- Berkshire East Mountain Resort
- Brimfield State Forest
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Bright Nights at Forest Park
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Canterbury Farm
- Clarksburg State Park
- Ekwanok Country Club