Holiday houses in Webster

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Quick stats about holiday rentals in Webster

  • Total holiday rentals

    Explore 10 holiday rentals in Webster

  • Nightly prices starting at

    Webster holiday rentals start at $156 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Webster holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Webster rentals

  • 4.9 Average rating

    Webster stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Webster

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

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Top Guest favourite
Cottage in Thompson
4.99 out of 5 average rating, 184 reviews

Peaceful Lakehouse | Thompson CT | Gorgeous Views

Escape to our beautifully renovated 1928 cottage on Quaddick Lake—your perfect retreat for relaxation and adventure. Just 60 minutes from Boston, Providence, and Hartford, this lakeside haven makes vacationing effortless. Start your day sipping coffee as the sunrise glows over the water and spend evenings by the crackling fire pit under the star filled sky. Whether paddling the lake or unwinding in cozy comfort, you'll feel miles away from the busy world, free to relax and make lasting memories.

Top Guest favourite
The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.
Farm stay in Thompson
5.0 out of 5 average rating, 257 reviews

Rustic Farmette Studio w/yearround 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.

Superhost
Cottage in Dudley
4.85 out of 5 average rating, 52 reviews

Cozy, 3BR lake-side retreat and outdoor oasis

Escape to our peaceful private lakefront cottage in Dudley, MA, your perfect year-round retreat! Recently updated 3-bed, 2-bath home on beautiful Pierpoint Meadow Lake offers swimming, fishing, kayaking, vibrant fall colors, and winter ice skating. Inside, enjoy air conditioning, cozy fireplace, dishwasher, washer/dryer, and new TVs. Outside, relax on the new multi-level deck with stunning lake views, gather by the fire pit, or step onto your private dock and sandy beach to make lasting memories

Top Guest favourite
A calm pond is depicted, surrounded by lush greenery and trees. Sunlight reflects off the water, creating a shimmering effect. Lily pads are visible on the surface, with a rustic stone pier in the foreground, adding a natural touch to the serene landscape.
Cabin in Thompson
4.98 out of 5 average rating, 180 reviews

Secluded cabin w/ Finnish Sauna & Forest Baths

A secluded, romantic, rustic, cabin alongside the French River - Frog Hollow is a perfect place to get away and experience the luxury of a wood fired sauna and forest baths. Located in the Quiet Corner of CT, relax as you watch the ducks, herons, turtles, and beavers along the river. Cook a delicious meal in the porch-enclosed kitchen, cozy up next to the woodstove fireplace, work remotely with a water view, or go for a paddle on the river. Ideal for a couple or solo traveler wanting to unwind.

Top Guest favourite
A charming in-law suite stands in a serene setting, surrounded by open grassy fields. The house features a wraparound porch and carefully landscaped flower beds, framed by trees that provide a natural boundary. The driveway leads toward the entrance, welcoming visitors to a peaceful retreat.
Apartment in Thompson
4.99 out of 5 average rating, 72 reviews

Acoustical Haven: Unwind & Unplug

Welcome to the Quiet Corner of Northeast CT! Acoustical Haven is a beautiful in-law suite with all the amenities needed to make your stay here comfy, relaxing and peaceful. Only an hour away from Providence, Boston or Hartford, explore all that the Last Green Valley has to offer: downtown Putnam's Antique district, Thompson Dam's lake and hiking trails, Thompson Speedway, wine and beer tastings, or simply relax on Acoustical Haven's 8 acres of tranquility. All are welcome at Acoustical Haven.

Guest favourite
A vibrant sunset paints the sky in hues of pink, orange, and purple above a tranquil lake. The water reflects the colorful sky, creating a serene atmosphere. Silhouettes of trees line the horizon, enhancing the peaceful view.
Home in Webster
4.86 out of 5 average rating, 132 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.

Guest favourite
The renovated house is situated amidst lush greenery, surrounded by trees and a well-maintained lawn. A small swimming pool is visible within a fenced area, complemented by several umbrellas for shade, enhancing the outdoor ambiance on a sunny day.
Home in Woodstock
4.92 out of 5 average rating, 273 reviews

Cedar Ridge: House

HOUSE in CT’s Quiet Corner: Renovated house bathed in light, with nice stunning hilltop views. Relax on its patios and small swimming pool, stroll along its forest paths, Located in New England's "Last Green Valley National Heritage Corridor" offers multiple attractions, home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities. NOTE: RENTED DOWNSTAIRS APARTMENT. OWN PRIVATE ENTRANCE. DOES NOT SHARE OUTDOOR SPACE, PATIO, OR POOL

Top Guest favourite
A spacious living area showcases large windows that invite natural light and views of the surrounding landscape. Comfortable seating includes a couch and armchair, complemented by a decorative fish tank. A dining table is visible in the background, enhancing the open and airy atmosphere.
Guest suite in Uxbridge
5.0 out of 5 average rating, 325 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Guest favourite
A feature wall is adorned with various steampunk elements, including gears, clocks, and unique decorative items. An intricately designed aircraft model is suspended from the ceiling, while a small table with a glass sits nearby, adding to the eclectic ambiance.
Farm stay in Thompson
4.94 out of 5 average rating, 254 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.

Top Guest favourite
An enclosed porch features large windows providing a view of the lake. Three booths with smooth surfaces are arranged along the space, inviting relaxation and dining while enjoying the surroundings. The flooring is made of natural wood, complementing the overall design.
Apartment in Webster
5.0 out of 5 average rating, 51 reviews

Webster MA on the Lake 1 Bedroom.

Lake Chargoggagoggmanchauggagoggchaubunagungamaugg. Private entrance. Enclosed porch right off the living area with 3 booths for crafting, eating and relaxing. An open patio & small yard space for games & picnic table and a solo stove. 80 ft of shore line, which is ideal for kids swimming/fishing, a beach toilet & gazebo. 4 Kayak's, 2 paddleboards, and a pedal boat are available for guest use with swimming ability.

Guest favourite
A close-up of a wooden patio table is shown, featuring a central hole for an umbrella. In the background, the tranquil lake reflects the overcast sky, flanked by trees and developed areas along the shore.
Home in Webster
4.92 out of 5 average rating, 39 reviews

Webster Lake - One Home / Two Apartments

Imagine the possibilities! Perfect for large families, multiple groups, or those simply craving extra space and privacy, this unique home offers the best of both worlds: two separate, fully equipped apartments under one roof! Whether you're planning a multi-generational getaway, a reunion with friends, or need separate quarters for your group, this property provides unparalleled flexibility.

Superhost
The spacious barn loft features a wooden floor and a high ceiling, accented by wooden paneling on the walls. A cozy bed is paired with a lounge area containing a sofa. A staircase leads to an upper loft space, with modern lighting fixtures visible above.
Barn in Thompson
4.86 out of 5 average rating, 21 reviews

Charming Barn Loft with Modern Comforts

Welcome to this cozy barn loft in Thompson, CT! This charming space offers a warm blend of rustic and modern design, perfect for a peaceful getaway. Featuring a spacious loft, hardwood floors, a full kitchen with retro appliances, and a stylish living area with a large TV. Relax in comfort and enjoy a serene atmosphere. Perfect for couples, small families, or solo travelers!

Popular amenities for Webster holiday rentals

Frequently Asked Questions

  • 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.

  • 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.

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

    Experience the best of Webster with our house rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • Do house rentals in Webster have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Webster. Enjoy a tailored experience with all the comforts you desire.

  • 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.