Vacation rentals in Rutland

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Top-rated vacation rentals in Rutland

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

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Guest favorite

Cottage in Worcester

4.87 out of 5 average rating, 107 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

Cottage in Petersham

4.99 out of 5 average rating, 153 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

Guest suite in Thompson

4.98 out of 5 average rating, 120 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

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 Wilton

4.95 out of 5 average rating, 576 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Guest favorite

Guesthouse in New Ipswich

4.94 out of 5 average rating, 300 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, 272 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.

Superhost

Guest suite in Worcester

4.89 out of 5 average rating, 395 reviews

Private Suite with separate entrance in Worcester

This private suite permits a maximum of two pets per reservation for $50 per a pet. The privacy is second to none, from check in to check out with private entrance gate. The living room has variety of books in 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.

Guest favorite

Home in Ware

4.87 out of 5 average rating, 117 reviews

Little House Inn - Private House - Secluded

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, 301 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

Cottage in Orange

4.94 out of 5 average rating, 133 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

Farm stay in Woodstock

4.98 out of 5 average rating, 170 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.