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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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
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 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.

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.

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.

Top Guest favourite
A serene lake view is captured at twilight, with soft clouds reflecting in calm waters. Soft lights from nearby docks and boats twinkle in the distance, creating a peaceful ambiance. A yellow inflatable is anchored nearby, and the scene is framed by the gentle curve of the hot tub.
Cottage in Mendon
4.95 out of 5 average rating, 147 reviews

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

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

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
The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.
Farm stay in Woodstock
4.98 out of 5 average rating, 230 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.

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 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.

Top Guest favourite
A spacious deck extends over the lake, featuring two comfortable chairs positioned for serene views. Lush greenery surrounds the area, and the calm water reflects the deck's inviting atmosphere. A white railing enhances safety while offering unobstructed access to the water.
Cottage in Sturbridge
4.92 out of 5 average rating, 182 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.

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.