Holiday rentals in Webster

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Top-rated holiday rentals in Webster

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Guest favourite

Flat in Woodstock Valley

4.93 out of 5 average rating, 334 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Spring into the warm weather of April and May. 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!! Woodstock Valley Country within two miles!

25 Apr – 2 May

$182 SGD per night

Guest favourite

Guest suite in Uxbridge

5.0 out of 5 average rating, 268 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.

26 Sep – 3 Oct

$190 SGD per night

Guest favourite

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!

23–30 Jul

$202 SGD per night

Guest favourite

Guest house in Uxbridge

5.0 out of 5 average rating, 122 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.

10–17 Mar

$220 SGD per night

Guest favourite

Farm stay in Thompson

4.94 out of 5 average rating, 159 reviews

Wizard's Roost at 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.

10–17 Sep

$157 SGD per night

Guest favourite

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.

15–22 May

$547 SGD per night

Guest favourite

Guest suite in Warren

4.95 out of 5 average rating, 265 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.

13–20 Oct

$97 SGD per night

Guest favourite

Tiny home in Smithfield

4.97 out of 5 average rating, 590 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.

12–19 Aug

$199 SGD per night

Guest favourite

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.

26 Jul – 2 Aug

$267 SGD per night

Guest favourite

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.

20–27 Nov

$186 SGD per night

Guest favourite

Flat in Dudley

4.82 out of 5 average rating, 352 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.

29 Oct – 5 Nov

$111 SGD per night

Guest favourite

Cabin in Webster

4.92 out of 5 average rating, 144 reviews

The Camp

We are in the Tri-State area, an hour west of Boston, 25 minutes South of Worcester. Nothing beats Lake living...the sunsets, the backyard to play badminton or croquet, kayaking, canoeing, the paddle boating, SWIMMING, having a camp fire or going to the city! Your cabin OF 650sq. ft. Is next to my home and steps to our beach. WiFii, one tv with ROKU.

8–15 Oct

$193 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Webster holiday 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 holiday rentals in Webster

Guest favourite

Guest suite in Uxbridge

4.98 out of 5 average rating, 133 reviews

The 1780 Suite

15–22 Oct

$141 SGD per night

Guest favourite

Cottage in Thompson

4.98 out of 5 average rating, 112 reviews

Private waterfront cottage on Quaddick Lake, CT

6–13 Sep

$352 SGD per night

Superhost

Flat in Worcester

4.89 out of 5 average rating, 391 reviews

Private Suite with separate entrance in Worcester

8–15 Dec

$112 SGD per night

Guest favourite

Farm stay in Southbridge

4.98 out of 5 average rating, 163 reviews

High Grass Farm

21–28 Sep

$237 SGD per night

Guest favourite

Flat in Webster

5.0 out of 5 average rating, 15 reviews

1 BR on Webster Lake.

19–26 Jul

$279 SGD per night

Superhost

Home in Webster

5.0 out of 5 average rating, 15 reviews

Newly Renovated Waterfront Lake House w/ Docks

15–22 Aug

$474 SGD per night

Guest favourite

Flat in Webster

5.0 out of 5 average rating, 14 reviews

Amazing Webster Lake Views and Private Oasis

14–21 Mar

$292 SGD per night

Guest favourite

Flat in Thompson

4.97 out of 5 average rating, 31 reviews

Acoustical Haven: Unwind & Unplug

27 Jun – 4 Jul

$276 SGD per night

Show all

Quick stats about holiday 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	$54 SGD before taxes and fees

Holiday rentals in Webster

Top-rated holiday rentals in Webster

Flat in Woodstock Valley

Guest suite in Uxbridge

Guest suite in Thompson

Guest house in Uxbridge

Farm stay in Thompson

Home in Webster

Guest suite in Warren

Tiny home in Smithfield

Farm stay in Thompson

Farm stay in Woodstock

Flat in Dudley

Cabin in Webster

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Webster holiday rentals

Stay near Webster's top sights

Other great holiday rentals in Webster

Guest suite in Uxbridge

Cottage in Thompson

Flat in Worcester

Farm stay in Southbridge

Flat in Webster

Home in Webster

Flat in Webster

Flat in Thompson

Quick stats about holiday rentals in Webster

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore