Winchester fishing vacation rentals

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winchester vacation rentals

Lake side house rentals in Winchester

Top guest favorite
Home in Ludlow
5 out of 5 average rating, 111 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

AmyRating, 5 stars6 days ago
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!
Guest favorite
Home in Londonderry
4.99 out of 5 average rating, 135 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

GeorgiaRating, 5 stars6 days ago
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!
Guest favorite
Home in Westminster
4.83 out of 5 average rating, 156 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

ElizabethRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Washington
5 out of 5 average rating, 103 reviews

Newer Home on quiet 200 acre lake - sleeps 6

ChrisRating, 5 stars1 week ago
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.
Top guest favorite
Home in Poultney
4.94 out of 5 average rating, 328 reviews

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs

MadisonRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Weare
4.97 out of 5 average rating, 103 reviews

Private Lake Front Home

IsabelaRating, 5 stars6 days ago
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!
Superhost
Home in South Londonderry
4.86 out of 5 average rating, 156 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

MarcosRating, 5 stars1 week ago
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.
Guest favorite
Home in Poultney
4.94 out of 5 average rating, 131 reviews

VT Lake House living with sunset views!

MadisonRating, 5 stars1 week ago
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

Guest favorite
Home in Westminster
4.94 out of 5 average rating, 128 reviews

Wachusett Mountain Get-Away

VanessaRating, 5 stars1 month ago
House was very nice and was perfect for us. Location was convenient to the activities we were attending. Thank you!
Top guest favorite
Home in Jaffrey
4.97 out of 5 average rating, 76 reviews

Willow Falls Home ~Hot tub & Waterfront

JoyRating, 5 stars1 week ago
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!
Top guest favorite
Home in Belchertown
4.99 out of 5 average rating, 71 reviews

Moonstone Lake House – romantic, serene, fun!

JohnRating, 5 stars6 days ago
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.
Top guest favorite
Home in Sunapee
4.97 out of 5 average rating, 197 reviews

@SunapeeSeasons—Across from Dewey Beach, Lake View

AkshayRating, 5 stars1 day ago
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.
Guest favorite
Home in Chesterfield
4.95 out of 5 average rating, 56 reviews

The River House

ColinRating, 5 stars1 week ago
Would love to come back some day, great trip
Guest favorite
Home in Mont Vernon
4.95 out of 5 average rating, 187 reviews

Private Waterfront! Views, Hot Tub, King Bed

GeoffreyRating, 5 stars1 month ago
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.
Guest favorite
Home in Orange
4.96 out of 5 average rating, 79 reviews

Four Season Cozy Cottage on Lake Mattawa

CricketRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars6 days ago
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

Superhost
Cabin in Fitzwilliam
4.83 out of 5 average rating, 147 reviews

Cozy Log Cabin Mountain Views

ElizabethRating, 5 stars1 month ago
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!
Top guest favorite
Farm stay in Warwick
4.97 out of 5 average rating, 66 reviews

Be Still Meadows at Chase Hill Farm - first floor

SusanRating, 5 stars3 months ago
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.
Guest favorite
Cabin in Guilford
4.96 out of 5 average rating, 71 reviews

Guilford Grove Cottage

ElizabethRating, 5 stars5 days ago
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.
Top guest favorite
Barn in Guilford
4.99 out of 5 average rating, 126 reviews

The Carriage Barn

AristidesRating, 5 stars1 week ago
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.
Top guest favorite
Guesthouse in Guilford
5 out of 5 average rating, 40 reviews

Peaceful forest cottage getaway

CourtneyRating, 5 stars6 days ago
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!!
Top guest favorite
Apartment in Dublin
4.97 out of 5 average rating, 232 reviews

Private Dublin apartment nestled in the woods

DianeRating, 5 stars2 weeks ago
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!
Guest favorite
Cottage in Brattleboro
4.97 out of 5 average rating, 31 reviews

On the Water at North Bridge Cove

StephRating, 5 stars2 weeks ago
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!
Top guest favorite
Guesthouse in Dummerston
5 out of 5 average rating, 16 reviews

Cottage amongst the trees

MattRating, 5 stars1 week ago
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.

Destinations to explore