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Vacation rentals in Webster

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Top-rated vacation rentals in Webster

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

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Farm stay in Southbridge

4.89 out of 5 average rating, 316 reviews

Scandanavian Wigwam with Sauna and Forest Baths

Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!

Guest suite in Uxbridge

4.99 out of 5 average rating, 321 reviews

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.

Rental unit in Woodstock Valley

4.93 out of 5 average rating, 380 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

Welcome to the scenic Northeast corner of Ct on beautiful Lake Bungee. Enjoy direct waterfront with stunning sunrises . 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 stars. BBQ propane grill. Stroll around both lakes . Enjoy bird sightings, nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility !!

Farm stay in Thompson

4.99 out of 5 average rating, 162 reviews

Rustic Farmette Studio w/ Pool and Hot Tub

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, or a family with a young kid. Please include all individuals (&pets) in your booking.

Guest suite in Uxbridge

4.99 out of 5 average rating, 169 reviews

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 suite in Thompson

4.99 out of 5 average rating, 143 reviews

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 suite in Uxbridge

4.99 out of 5 average rating, 194 reviews

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 suite in Worcester

4.88 out of 5 average rating, 418 reviews

Private Suite with separate entrance in Worcester

This private suite allows a maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance gate. The living room has a mini library for guests, 55" TV with Internet streaming channels and fully subscribed YouTubeTv. The suite also has a mini kitchen with a refrigerator, a freezer, a microwave, air fryer, omelet egg maker and coffee maker. It also has fully stocked linen closet and electric pump air mattress if necessary.

Farm stay in Thompson

4.96 out of 5 average rating, 171 reviews

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.

Farm stay in Woodstock

4.98 out of 5 average rating, 187 reviews

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.

Rental unit in Dudley

4.84 out of 5 average rating, 421 reviews

웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT

Excellent for couples; voyagers & professionals. Ideal for short or long terms stays, everything is incld. Cozy, bright and small very comfy bedroom, if business travel or just visiting the area, Kitchen, living room and Laptop Desk. Self-Check-In, Wi-Fi, free & safe on-street Parking, Lock on Door, Laundry available*, A/C, we are in a busy street during the day but really safe.

Bungalow in Pomfret

4.96 out of 5 average rating, 112 reviews

Pomfret private bungalow

Visit our cozy woodland bungalow for your next trip to Pomfret CT. Located on RT 244. 3.5 miles from Pomfret School and 5.2 miles from Woodstock Academy. High speed internet and cable TV. Enjoy your evenings around the fire pit. Full kitchen with all appliances and utensils required for any meal. Full access to over 2 acres of woods. Washer and Dryer.

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Popular amenities for Webster vacation rentals

Free parking on premises

Air conditioning

Stay near Webster's top sights

Indian Ranch10 locals recommend

Point Breeze9 locals recommend

Mexicali Grill9 locals recommend

The Lodge Restaurant5 locals recommend

Mohegan Bowl4 locals recommend

Samuel Slater's Restaurant3 locals recommend

Other great vacation rentals in Webster

Rental unit in Webster

5 out of 5 average rating, 22 reviews

Amazing Webster Lake Views and Private Oasis

Rental unit in Killingly

4.93 out of 5 average rating, 95 reviews

2 Bedroom, 1st floor apartment

Rental unit in Webster

5 out of 5 average rating, 31 reviews

1 BR on Webster Lake.

Cottage in Petersham

4.99 out of 5 average rating, 179 reviews

Cider House Cottage

Rental unit in Thompson

4.98 out of 5 average rating, 48 reviews

Acoustical Haven: Unwind & Unplug

Guest suite in Thompson

4.96 out of 5 average rating, 54 reviews

Trees, pond, and wildlife in its entire splendor

Home in Webster

4.92 out of 5 average rating, 25 reviews

Webster Lake - Main Apartment 3BR / 2BATH

Rental unit in Sutton

4.81 out of 5 average rating, 62 reviews

Spacious, 1 bedroom, full kitchen and laundry.

Quick stats about vacation rentals in Webster

Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
780 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

Do house rentals in Webster have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Webster. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Webster?
Experience the best of Webster with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Webster?
Webster has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Webster?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Where should I stay in Webster?
Make yourself at home in Webster by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in East Village, over 10 vacation rentals in Main Street Historic District, and over 10 vacation rentals in North Village.
Are there vacation rentals with a dedicated workspace in Webster?
Yes! Work meets play with ease at over 10 vacation rentals in Webster featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore