Vacation rentals in Webster

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Top-rated vacation rentals in Webster

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Guest favorite

Guest suite in Uxbridge

5.0 out of 5 average rating, 273 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.

Sep 2 – 9

G$29,233 GYD per night

Guest favorite

Apartment in Woodstock Valley

4.93 out of 5 average rating, 336 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

UCONN Graduations coming soon, celebrate, relax. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. Pretty flowers, trees surrounding!! Now open-Woodstock Valley Country Store

Feb 11 – 18

G$33,981 GYD per night

Guest favorite

Guest suite in Thompson

4.98 out of 5 average rating, 114 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!

Aug 23 – 30

G$31,033 GYD per night

Guest favorite

Guesthouse in Uxbridge

5.0 out of 5 average rating, 123 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.

Aug 27 – Sep 3

G$33,660 GYD per night

Guest favorite

Farm stay in Thompson

4.94 out of 5 average rating, 161 reviews

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.

Oct 4 – 11

G$23,989 GYD per night

Guest favorite

Home in Webster

4.86 out of 5 average rating, 110 reviews

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.

Jun 4 – 11

G$83,826 GYD per night

Guest favorite

Guest suite in Warren

4.95 out of 5 average rating, 266 reviews

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.

Nov 9 – 16

G$14,926 GYD per night

Guest favorite

Tiny home in Smithfield

4.97 out of 5 average rating, 595 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Nov 2 – 9

G$32,438 GYD per night

Guest favorite

Guest suite in Uxbridge

4.99 out of 5 average rating, 135 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 has been restored and updated by two generations of architects in the family. 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.

Feb 7 – 14

G$21,669 GYD per night

Guest favorite

Farm stay in Thompson

4.99 out of 5 average rating, 133 reviews

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.

Aug 19 – 26

G$41,010 GYD per night

Guest favorite

Farm stay in Woodstock

4.98 out of 5 average rating, 168 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.

Jul 25 – Aug 1

G$28,596 GYD per night

Guest favorite

Apartment in Dudley

4.82 out of 5 average rating, 353 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.

Oct 25 – Nov 1

G$16,926 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Webster vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Webster's top sights

Indian Ranch10 locals recommend

Point Breeze9 locals recommend

Mexicali Grill9 locals recommend

Mohegan Bowl4 locals recommend

Bistro Eighty Ates3 locals recommend

The Lodge Restaurant5 locals recommend

Other great vacation rentals in Webster

Guest favorite

Apartment in Worcester

4.89 out of 5 average rating, 392 reviews

Private Suite with separate entrance in Worcester

Nov 6 – 13

G$16,922 GYD per night

Guest favorite

Farm stay in Southbridge

4.98 out of 5 average rating, 164 reviews

High Grass Farm

Dec 23 – 30

G$36,704 GYD per night

Superhost

Cottage in Scituate

4.9 out of 5 average rating, 196 reviews

5 Star cottage in historical Clayville

Jun 17 – 24

G$24,455 GYD per night

Guest favorite

Cottage in Thompson

4.98 out of 5 average rating, 112 reviews

Private waterfront cottage on Quaddick Lake, CT

Sep 6 – 13

G$53,950 GYD per night

Guest favorite

Guesthouse in Killingly

4.97 out of 5 average rating, 116 reviews

The Carriage House at Chaprae Hall

Sep 27 – Oct 4

G$27,753 GYD per night

Guest favorite

Farm stay in Southbridge

4.89 out of 5 average rating, 291 reviews

Scandanavian Wigwam with Sauna and Forest Baths

Jul 9 – 14

G$30,985 GYD per night

Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 149 reviews

Cider House Cottage

Jun 10 – 17

G$29,994 GYD per night

Guest favorite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

Mar 1 – 8

G$15,368 GYD per night

Show all

Quick stats about vacation rentals in Webster

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
650 reviews
Nightly prices starting at
G$8,342 GYD before taxes and fees

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 $60 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 air conditioning, over 10 homes with wifi, 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 North Village, and over 10 vacation rentals in Main Street Historic District.
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.

Vacation rentals in Webster

Top-rated vacation rentals in Webster

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Webster vacation rentals

Stay near Webster's top sights

Other great vacation rentals in Webster

Apartment in Worcester

Farm stay in Southbridge

Cottage in Scituate

Cottage in Thompson

Guesthouse in Killingly

Farm stay in Southbridge

Cottage in Petersham

Guest suite in Brooklyn

Quick stats about vacation rentals in Webster

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Webster have air conditioning?

How much does it cost to stay in house rentals in Webster?

Are there family-friendly vacation rentals in Webster?

What are the most popular amenities for House Rentals in Webster?

Where should I stay in Webster?

Are there vacation rentals with a dedicated workspace in Webster?

Destinations to explore