Vacation rentals in Rutland

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Top-rated vacation rentals in Rutland

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Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 149 reviews

Cider House Cottage

Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.

Guest favorite

Cottage in Worcester

4.87 out of 5 average rating, 106 reviews

Unique and Private Cottage in Worcester

Unique and private - your own cottage in the desirable West Side of Worcester. The carriage house of a larger property, the cottage is situated in lush gardens, with on-street parking on your doorstep. 5 minute walk to WPI, 5 minute drive to city center and 15 mins to UMass Med. Furnished tastefully and simply with antiques and original art works; brand-new bathroom with shower; washer and dryer; fully-equipped kitchen. An ideal retreat or longer professional let - fast Eero mesh wifi network.

Guest favorite

Guesthouse in Worcester

4.81 out of 5 average rating, 207 reviews

Carriage house apartment

We have a one bedroom apartment at our historic home, Liberty Farms, which is the 2nd oldest house in Worcester Massachusetts. Also well known as the Abby Kelley Foster house to the locals. The full kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer & dryer. Guests may enjoy the patio and grounds in the quiet Tatnuck Square area, conveniently located minutes from the Worcester Regional Airport, restaurants, and hiking trails. House tours upon request.

Guest favorite

Guest suite in Ashburnham

4.99 out of 5 average rating, 404 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Guest favorite

Guesthouse in New Ipswich

4.94 out of 5 average rating, 296 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out at, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person rentals. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome!

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.

Guest favorite

Home in Oakham

5.0 out of 5 average rating, 145 reviews

Lovely & Peaceful Waterfront Vacation Retreat

Come enjoy this unique & beautiful retreat home, set on 50 acres of wooded land, with a breath-taking view over a 2 mile long, 190-acre body of water, & no houses in sight! Wonderful in any season. Peaceful, healing haven, & great get-away spot for a romantic weekend or family vacation. Perfect for swimming, boating, fishing, hiking, & cross-country skiing--or just relaxing in a hammock, on the deck, or in a bedroom overlooking the water. Youtube Video: Fred's Place, James Crowther

Guest favorite

Home in Ware

4.89 out of 5 average rating, 110 reviews

Little House Inn

NO CLEANING FEES - NO CHORE LIST Reconnect with loved ones in this family-friendly place. Our little house is situated on an acre and a half of land surrounded by wetlands and woods yet minutes from local colleges and amenities. Enjoy the beautiful night sky while relaxing by the fire pit. Or enjoy the woodland view from your deck with your morning coffee. Deer, turkeys, bunnies, and many native birds are regular visitors. Check out our guidebook for places to eat & things to do.

Guest favorite

Guesthouse in Westminster

4.98 out of 5 average rating, 291 reviews

Guest House - 4 miles from Wachusett Mt.

Enjoy your stay in this cozy, newly renovated semi-attached in-law unit. It is located close to Route 2, walking distance to the town center, only 4 miles from Mt. Wachusett in a quiet neighborhood. It has 2 parking spaces and a private entrance. This unique space has everything to make you feel at home – including WiFi and Netflix. The kitchen is equipped with a Keurig Coffee Maker, Mini Fridge, and a Microwave. Queen-size bed, fresh towels, body wash are also provided.

Guest favorite

Barn in Holden

4.9 out of 5 average rating, 378 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll through our Lavender Labyrinth and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Guest favorite

Cottage in Orange

4.94 out of 5 average rating, 131 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Guest favorite

Apartment in Worcester

4.89 out of 5 average rating, 392 reviews

Private Suite with separate entrance in Worcester

This private suite has a quiet vibe. The privacy is second to none, from check in to check out with private entrance gate. The living room has variety of books at the guests library, 55" TV with Internet streaming channels and fully subscribed YouTubeTv. The main bedroom has a refrigerators, brand new air fryer, air filter and humidifier, Keurig coffee maker and a vacuum cleaner. Also the apartment has a full private bathroom and patio.