Vacation rentals in West Dudley

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Top-rated vacation rentals in West Dudley

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Top guest favorite

Cottage in Thompson

4.99 out of 5 average rating, 140 reviews

Waterfront Cottage in Thompson CT • Dogs Welcome

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.

Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 238 reviews

Cedar Ridge: House or House+Apartment

2 OPTIONS: HOUSE or HOUSE+APARTMENT In CT’s Quiet Corner: renovated 2-level house bathed in light, with nice flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.

Guest favorite

Apartment in Woodstock

4.86 out of 5 average rating, 44 reviews

Woodstock Red Barn | Private Apt in Idyllic Town

This studio apt offers you a comfortable & quiet stay in pastural Woodstock. Surrounded by rolling hills & dairy farms, this spacious & completely private apt is the perfect place for a weekend retreat. Whether that means exploring the quaint towns that make up the quiet corner or taking time to escape the day to day & recharge, this rental has you covered. You will enjoy complete privacy in this detached dwelling w/ a private entrance & self-checkin. It also features free parking, WiFi & A/C.

Top guest favorite

Guest suite in Uxbridge

4.97 out of 5 average rating, 191 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.

Top guest favorite

Guest suite in Thompson

4.99 out of 5 average rating, 159 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 favorite

Home in Southbridge

4.93 out of 5 average rating, 374 reviews

Charming Cape--Kid & Dog Friendly 🐾

Old style cape, newly renovated. Lots of vintage charm with new upgrades. Beautiful, 3 bedroom, 1.5 bath & full kitchen. Kitchen is fully stocked with duel kuereg and drip coffee pot & Ninja blender. Beautiful touches throughout to make your stay cozy. EXTRAS INCLUDE : 24-HOUR CHECK-IN / keyless entry FREE COFFEE FREE Oatmeal bar HIGH SPEED WI-FI Pack N Play Glider for nursing/feeding moms! SMART TVs in 2 bedrooms Enjoy a cute stay in quiet neighborhood, 7 minutes from Sturbridge exit (84).

Top guest favorite

Guest suite in Woodstock

5 out of 5 average rating, 11 reviews

Luxe, private, separate Suite in peaceful setting!

Calendar just opened for May & June! Luxurious, sun-filled 1-BR In-Law Suite with private bath, Living Room, Porch & separate entry. Country setting 2-minutes from one of North America's "Top 10 Scenic Byways!" Living Room w/ paneled fireplace, screened Porch, equipped Kitchen. Spacious tiled Bath with shower. Inviting bluestone Patio & heated, gunite salt-water pool. Near farms/markets, antique shops, restaurants. Centrally located 1-hour from Boston, Hartford, Providence & the CT Shore!

Top guest favorite

Home in Scituate

4.98 out of 5 average rating, 144 reviews

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. Pool has surcharge $20 if weather is good during your stay.

Top guest favorite

Guest suite in Warren

4.95 out of 5 average rating, 301 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.

Top guest favorite

Apartment in Brimfield

4.98 out of 5 average rating, 170 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

Top guest favorite

Guest suite in Uxbridge

5 out of 5 average rating, 239 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.

Superhost

Home in Putnam

4.77 out of 5 average rating, 239 reviews

Calm & Cozy House in a Quiet Corner

The perfect place to get away to enjoy a Best Kept Secret of New England. You will have access to the whole house during your stay. All on one level (ground floor). Enjoy the relaxing view of the field, red barn and Quinnebaug River while snuggling up with read a book. The country kitchen is complete with refrigerator, toaster, oven, microwave, and coffee maker. The best of Putnam Antique District, Entertainment, Dining, Nightlife and shopping a 4 minute drive away.

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Other great vacation rentals in West Dudley

Apartment in Woodstock

5 out of 5 average rating, 6 reviews

Quiet Corner Studio

ShawnRating, 5 stars2 weeks ago

Karin and Jom have a beautiful small apartment that was perfect for a kid-free getaway for my wife and I. communications great, the space was lovely and see their highland cows out the windows was lovely. we also loved their friendly pouches. wed go back in a heartbeat and had a great time. if you're looking for a quiet place to unplug and relax this is it!!!

Guest favorite

Apartment in Ashford

4.96 out of 5 average rating, 176 reviews

On The Run Farm

EurídiceRating, 5 stars2 weeks ago

Perfect for a get away. Everything looks beter than the pictures. Clean and very comfortable. Laurie is an excellent host, very creative to make us feel comfortable. Next time I need a place to stay in Connecticut, I hoop this one is available.

Guest favorite

Home in Woodstock

4.96 out of 5 average rating, 46 reviews

Mid-Century Modern Lakefront Cabin

JacquieRating, 5 stars1 week ago

If you’re looking for a serene and restful place to come “home” to after a day out and about…this is the place to stay! The central location allowed us to easily check out Boston, Newport and several Connecticut spots...including a winery & brewery only 10 min away! We also enjoyed down days simply relaxing at Erin’s place….by the fire, lounging by the water or taking a paddle around the lake. And anything you could think of they had…sweatshirts and blankets for outside by the fire, games, fully stocked kitchen for making meals in, steam shower, office space, and more. Our family of four (with adult children) had plenty of space to spread out and have time for ourselves, too. I also really like the mid-century modern decor…very nice touch :) Erin and Jaiden were great hosts. They were very responsive and provided detailed instructions and ongoing communications to ensure our stay was going well. Thanks again!

Guest favorite

Apartment in Dudley

4.95 out of 5 average rating, 21 reviews

Artsy Barn in the Country

HaleyRating, 5 stars9 months ago

I stayed with friends for the September Brimfield Antiques Faire and had an incredible time. If you’re coming for the show, this place is a great option—the drive to Brimfield is about 30 minutes, but very easy and straightforward, and the Threadbare clothing and textiles show is only a few minutes’ drive down the main road. Monica was a great host and responded to our messages very quickly, bringing us things we requested and giving helpful instructions as needed. She keeps the place stocked with books, cassettes, games, etc. You can tell she put thought and care into making a great space for entertaining. The barn was bigger and nicer than expected based on the great price, and though the “bedrooms” were all connected, we each felt we had our own space and were able to decompress and sleep easily. The kitchen was stocked with most of what we needed to make our meals at home, and we had more than enough towels and bedding for all of us. I would definitely stay here again!

Guest favorite

Guest suite in Brooklyn

4.93 out of 5 average rating, 189 reviews

Affordable In-Law Apartment in Brooklyn, CT

KathyRating, 5 stars1 month ago

We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.

Top guest favorite

Home in Sturbridge

5 out of 5 average rating, 13 reviews

Tull Haus

LisaRating, 5 stars4 weeks ago

My family had a pleasant stay at Tull Haus. It was conveniently located near Brimfield and Salem. All 7 of us fit comfortably in the house and we were able to cook meals and sit down together around the dining area table. We recommend this house especially if you have a larger group.

Guest favorite