Holiday rentals in Windham County

Serenity Ashford Lake

Serenity Ashford Lake is truly a gem far from the hustle and bustle of everyday life, while still enjoying all the creature comforts. Situated on the shores of tranquil Ashford lake, the Serenity lake house is definitely your place to relax and unwind. Waterfront jacuzzi, gazebo, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your favorite books, relax, and enjoy lake time!

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Brookside Chalet

Not just a place to stay but a place where you will want to stay. - Dedicated parking space - Well-appointed full kitchen - Deck overlooking Mashamoquet Brook (our guests refer to it as the tree house:) The bed will be the highlight of your experience. This high quality queen is accessorized with a pillow top mattress, goose down and memory foam pillows and spa quality sheets and pillow cases. Location: - Five minute drive to Pomfret Prep. - Ten minute drive to main Street in Putnam.

SteamPunk Bunk House and Intergalactic Way Station

A farm stay like no other! The future is the past and the past is the future with STEAMPUNK details that delight at every turn. Feed the goats, walk the trails, meet an alien. A complete apartment great for longer stays. Enjoy the imagined history of this 1825 farm house. Enjoy New England without spending days driving. Come visit a simpler time where nature is just outside your door and ET is sharing the kitchen. Cook s'mores fireside or say hi to "blue" our resident heron.

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)