Vacation rentals in Rutland

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Top-rated vacation rentals in Rutland

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Top guest favorite

A bright bathroom features a clawfoot bathtub, creating a focal point against the deep red walls. Natural light filters through a window, illuminating the space. Woven rugs add texture to the wooden floor, while neatly arranged towels are visible on a nearby bench.

Cottage in Petersham

4.98 out of 5 average rating, 197 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

A modern bathroom features a spacious glass shower with a sleek transparent design. A textured rug in neutral tones lies on the tiled floor, complementing the clean lines of the cabinetry nearby. Natural light may be visible, enhancing the inviting atmosphere.

Guest suite in Ashburnham

4.98 out of 5 average rating, 466 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

An outdoor seating area is featured on a wooden deck, showcasing a light-colored sectional sofa with cushions and a matching coffee table. A grill stands nearby, surrounded by greenery, while a welcoming area rug anchors the space. Sunlight illuminates the deck, highlighting its wooden texture.

Guesthouse in Worcester

4.82 out of 5 average rating, 274 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 winter landscape showcases illuminated ski slopes on Wachusett Mountain, creating a visual contrast against the evening sky. The gentle slopes lead down to the base area, where buildings are warmly lit, presenting a welcoming atmosphere for visitors.

Home in Westminster

4.83 out of 5 average rating, 156 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 red tray is positioned on a light-colored dresser, containing a remote control and a white dish labeled 'TRINKETS'. The dish provides a dedicated space for small items, enhancing organization on the dresser.

Guest suite in Hubbardston

4.99 out of 5 average rating, 123 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

A large red barn-style building is featured, with wooden beams supporting the entrance. Visitors are seen making their way toward the entrance, adorned with seasonal decorations. The sky is filled with clouds that create a dramatic backdrop for this inviting farm setting.

Farm stay in Rutland

4.89 out of 5 average rating, 107 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 exterior view of the entrance to a building showcases wooden double doors adorned with various decorative signs and vintage license plates. The area is framed by greenery, with a paved driveway leading up to the doors, contributing to a rustic and welcoming appearance.

Guest suite in Warren

4.95 out of 5 average rating, 299 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 Ware

4.89 out of 5 average rating, 242 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 bright kitchen area is equipped with modern appliances, including a gas range and microwave. Light-colored cabinetry provides ample storage, and a dining table with a decorative table runner adds a touch of color. Natural light fills the space through the windows, enhancing the airy atmosphere.

Apartment in Worcester

4.97 out of 5 average rating, 34 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.

Top guest favorite

A sleek Keurig coffee maker is positioned on a dark countertop, accompanied by a transparent kettle and a glass canister filled with coffee pods. The modern appliances are set against a neutral grey wall, adding a contemporary touch to the space.

Guesthouse in Westminster

4.98 out of 5 average rating, 397 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!

Guest favorite

The stone barn building is framed by vibrant lavender fields in the foreground. Evening light illuminates the windows, while a calm sunset creates a soft gradient in the sky, transitioning from warm hues to deep blues.

Barn in Holden

4.89 out of 5 average rating, 466 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 around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Top guest favorite

A vibrant sunset casts a gradient of purple and orange hues across the sky, with silhouettes of trees visible in the foreground. The mountain range can be faintly discerned in the distance, providing a serene backdrop to the tranquil scene.

Home in Sterling

4.94 out of 5 average rating, 207 reviews

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

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Popular amenities for Rutland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Rutland

A comfortable living area features a gray sofa with decorative pillows and a round coffee table. A hanging chair adds a unique touch. Large glass doors allow natural light, and a rug complements the space. A TV is positioned against the wall, alongside a stylish cabinet.

Apartment in Worcester

4.64 out of 5 average rating, 14 reviews

Comfortable in Worcester!

BrieanneRating, 5 stars1 month ago

Stayed for one night, great place to stay. Neat and clean and host was very responsive

Guest favorite

The exterior of a charming three-story house is presented, featuring a blue facade with white trim. A covered porch adorned with decorative items enhances the welcoming entry. Lush greenery surrounds the property, and a pathway leads to the front door, suggesting easy access.

Apartment in Leicester

4.87 out of 5 average rating, 15 reviews

Sunny & Spacious 3BR, close to Worcester!

KirakiraRating, 5 stars1 day ago

Jeremiah & Kasie were helpful and accommodating! Great stay - spacious apartment for myself and my daughters. Great communication and helpful tips.

Guest favorite

A small balcony is featured with a round table and two teal chairs. Above, string lights adorn the railing, while greenery from nearby trees provides a natural backdrop. The bright blue sky adds a cheerful ambiance to the space.

Private room in Worcester

4.8 out of 5 average rating, 303 reviews

★Central, Historic location★ | Comfy Clean Relaxed

KennyaRating, 5 stars1 week ago

James was very communicative prior to check in and checked in on us to make sure we got in okay. The room was comfortable and as described and the place was easy to find.

Guest favorite

The kitchen features dark wood cabinetry and a central island with a countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. A window allows natural light to illuminate the workspace, and decorative items enhance the functional design.

Private room in Belchertown

4.96 out of 5 average rating, 84 reviews

Sunny room with private bathroom

VinciRating, 5 stars1 week ago

A really nice cozy room that's affordable and is just a great deal for a place to rest at night. the location is beautiful, and more importantly, quiet. would definitely comeback.

Top guest favorite

A cozy seating area features a striped sofa adorned with two patterned cushions. A glass-topped coffee table rests on a decorative rug, enhancing the space. The warm wooden flooring and a side lamp offer soft lighting, complemented by framed artwork on the wall.

Private room in Leominster

4.94 out of 5 average rating, 104 reviews

Private Leominster 3rd Floor Apartment

RajniRating, 5 stars1 week ago

I love Lenny’s Place and I’m so happy I found it. Lenny and his family are beautiful and good people. Lenny’s Mom Maria made me a beautiful dinner one evening I had asked for more towels and came home to find the towels and dinner. I grew up in Leominster but I hadn’t been back in 41 years. This was perfect for me and very close to town a 10 minute walk and a very short walk to Barrettes Pond right down the St. I used to swim there as a child. The surrounding area is stunning very green and many maple trees.

Guest favorite

An outdoor dining set is displayed on a wooden deck. The table is surrounded by six gray woven chairs. An umbrella provides shade over the table, which is adorned with a vase of flowers. A soft area rug sits beneath the table and chairs.

Private room in Leominster

4.81 out of 5 average rating, 118 reviews

HomeSweet Home#2 (Sorry we don’t take smokers)

FrancisRating, 5 stars1 month ago

it works well for someone looking for comfortable place to spend the night . Its a bedroom with everything you need including a microwave , refrigerator coffee and a tv . Real clean

Guest favorite