Vacation rentals in Rutland

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Top-rated vacation rentals in Rutland

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Top guest favorite

A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.

Cottage in Petersham

4.99 out of 5 average rating, 212 reviews

Cider House Cottage

Antique guest cottage on a becountry 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

Top guest favorite

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, 204 reviews

Rustic Farmette Studio w/Pool & 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 favorite

The exterior of The Ginger Bed is showcased, featuring a light green facade with white trim around the windows and door. A welcoming orange door is prominently displayed, surrounded by a landscaped area with colorful mums and autumn foliage.

Guest suite in Ashburnham

4.98 out of 5 average rating, 481 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

A two-story grey house with white trim is visible, featuring large windows and a front porch. A white car is parked in the driveway, leading to a closed garage door. Lush trees provide greenery around the property.

Guest suite in Worcester

4.88 out of 5 average rating, 455 reviews

Private Suite with separate entrance in Worcester

The suite allows maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance. The living room has mini library for guests, a 65 inch smart TV with high speed Internet and complimentary YouTubeTV local channels. The suite has a mini kitchen with mini refrigerator, freezer, microwave, air fryer, and coffee maker. It also has stocked cabinet utensils, cleaning supplies, linen closet and electric pump air mattress if necessary.

Guest favorite

A welcoming living room features light-colored sofas adorned with decorative pillows. Natural light filters through two windows, illuminating a cozy atmosphere. A lamp and a dresser add functionality, while a neutral carpet completes the space. Greeting from the entrance can be seen in the background.

Guesthouse in Worcester

4.83 out of 5 average rating, 292 reviews

Carriage house apartment

We have a one bedroom apartment at our historic home, Liberty Farm, which is the 2nd oldest house in Worcester Massachusetts and known as the Abby Kelley Foster house to the locals. Recent furniture upgrade in living room, see pictures. Kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer/dryer. Guests may enjoy the grounds in the quiet Tatnuck Square neighborhood, minutes from the Worcester Airport, restaurants, and hiking. House tours upon request.

Guest favorite

A charming lake house is depicted by the water, showcasing a light blue exterior and a welcoming front porch. The reflection in the calm lake adds depth to the scene, surrounded by lush greenery and hints of fall colors in the trees.

Home in Westminster

4.83 out of 5 average rating, 168 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Top guest favorite

A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.

Guest suite in Hubbardston

4.99 out of 5 average rating, 143 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

Guest favorite

Highland cattle and other animals are seen grazing on a lush green pasture under a clear blue sky. Rolling hills surround the field, creating a serene rural landscape filled with natural beauty.

Farm stay in Rutland

4.89 out of 5 average rating, 113 reviews

Spacious 3 Bedroom Home for Family Farm Stay

We welcome you to our farm to enjoy our scenery while making memories at our unique rental home great for groups. Our house rental is part of our property where we invite guests to escape to the farm. This family home is excellent for those looking to relax while away from the ski slopes or simply wanting a space to get away. In the middle of an area with plenty of outdoor activities nearby, we're only 8 miles from Wachusett Mountain Ski Resort and have restaurants within just minutes.

Top guest favorite

An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.

Loft in Peterborough

5 out of 5 average rating, 201 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Guest favorite

A decorative sign reading 'Little House Inn' is visible beneath a flowering tree. Circular images feature a cozy living area with multiple windows, scenic views of seasonal foliage, and tranquil outdoor spaces, highlighting the surrounding nature and inviting atmosphere.

Home in Ware

4.89 out of 5 average rating, 272 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.

Top guest favorite

A spacious living area highlights a comfortable gray sofa, complemented by a wooden coffee table at the center. A large television is mounted on the wall, and natural light enters through multiple windows adorned with white trim.

Apartment in Worcester

4.96 out of 5 average rating, 55 reviews

Centrally Located Apartment in Worcester

This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.

Guest favorite

A cozy living area features a large sectional sofa in gray, complemented by a bright yellow armchair. A modern black coffee table sits in the center. A flat-screen TV is mounted on the white wall, while warm string lights create a welcoming ambience.

Guesthouse in Westminster

4.98 out of 5 average rating, 423 reviews

Guest House - 4 miles from Wachusett Mt.

Welcome to a cozy, newly renovated semi-attached in-law unit! Nestled in a peaceful neighborhood, you’ll be just a short walk from the town center and only a 10-minute drive to the scenic Mount Wachusett. With easy access to Route 2, it’s the ideal base for your adventures. Enjoy the privacy of your own entrance and two dedicated parking spaces. Whether you’re here for a weekend getaway or a longer stay, we’re sure you’ll enjoy your time in this inviting space!