Vacation rentals in Webster

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Top-rated vacation rentals in Webster

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Guest favourite

Guest suite in Uxbridge

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Guest favourite

Farm stay in Southbridge

High Grass Farm

Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi). Our secluded setting on 19 acres in southern Mass is minutes from I-90 and I-84, and borders CT, Old Sturbridge Village and the Westville recreation area.

Guest favourite

Rental unit in Woodstock Valley

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Summer is here . Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. The sunrises are breathtaking. Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the moon & stars. BBQ propane grill. Enjoy scenic walks around both lakes . Enjoy swimming, a boat ride, bird sightings, nature’s finest. Great local dining, escape and enjoy “Tranquility “

Guest favourite

Guest suite in Thompson

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Guest favourite

Guest suite in Uxbridge

The 1780 Suite

Join us for a step back in time at our unique bucolic property. Set on a scenic road, the post and beam farmhouse was built in 1780 and offers a haven of peace and tranquillity after a busy day of exploring New England. Guests have a private entrance and wind their way up the period staircase to the second-floor suite with two bedrooms, a sitting room, a breakfast nook, and a bathroom. Enjoy your morning coffee outside on the Adirondack chairs as you contemplate the charms of country living.

Guest favourite

Guest suite in Uxbridge

Zen Inspired Private Suite with 2-mile Trail Loop

Zig-Zag Trails unique offering is a harmonious blend of modern comfort and the timeless allure of rural living. A newly built 1000 sq ft guest suite situated on over 65 acres of private meadows and forests with zig-zagging trails throughout, providing the ultimate getaway to relax and recharge. This property is a haven for nature lovers and homebodies alike. We are conveniently located in the heart of the Blackstone Valley, 1hr from Boston, 35min from Providence, and 25min from Worcester.

Guest favourite

Farm stay in Thompson

Wizard's Roost and Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

Guest favourite

Home in Webster

Webster Waterfront Cottage Nestled in the Pines

Light, bright sunny home nestled in the pines on a quiet dead end road. It's the perfect spot to relax, go swimming, kayaking, fishing or just sit on the dock and relax. There is an outdoor patio area overlooking the lake with a table/chairs, a gas grill for BBQs and a gas firepit for s'mores. Open kitchen/dining/living room with room to spread out. Kitchen has everything you need a Keurig, pots/pans, basic spices, garbage bags etc. AC in the 2 queen bedrooms, no AC in full bedroom.

Guest favourite

Guest suite in Warren

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

Guest favourite

Farm stay in Thompson

Rustic Farmette Studio w/ Hot Tub & seasonal pool

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, a small family. Please include all individuals (&pets) in your booking.

Guest favourite

Guesthouse in Killingly

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Guest favourite

Farm stay in Woodstock

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.