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, 199 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, 467 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 white picket fence gate provides access to a paved sidewalk leading into a private yard. The background features trees, and a utility shed is visible behind the fence. A sense of openness is created by the surrounding natural landscape.

Guest suite in Worcester

4.88 out of 5 average rating, 443 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

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, 276 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

Apartment in Fitchburg

5 out of 5 average rating, 24 reviews

Relaxing Poolside Getaway

Welcome to our charming 1-bed, 1-bath side-by-side unit, a perfect paradise with poolside access available during the warmer months! My husband and I, along with our cat, Mia, live in the main house. Enjoy the TVs in both the living room and bedroom, each offering streaming options, along with a fully equipped kitchen. The futon converts into a full-size bed for additional guests. It’s a great place to unwind, whether indoors or relaxing in the backyard setup. We look forward to hosting you!

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, 125 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

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, 35 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, 399 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

A spacious living area is highlighted by warm wooden floors and soft lighting. A comfortable gray sectional sofa faces a sleek fireplace, creating a cozy focal point. A bookshelf is visible in the corner, showcasing a variety of books, while an open door leads to another room.

Apartment in Shrewsbury

4.93 out of 5 average rating, 87 reviews

Clean & Cozy 2BR Across from Quinsigamond Lake

Unwind in our comfy 2-bedroom apartment with all the essentials for a comfortable stay. Work remotely while facing the lakeview. Super close to UMass Memorial, UMass campus, and just minutes away from Starbucks, Whole Foods, TraderJoe's and many more. Surrounded by many restaurants with great variety of taste. Easy access to the highway. Escape the ordinary and make this homy lakeview apartment your home away from home. Book now for a delightful experience!

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.

Guest favorite

An indoor swimming pool is surrounded by wooden walls and a ceiling of wood beams. Natural light enters through multiple windows, while lounge chairs are positioned nearby. The pool features a smooth surface, with steps leading into the water.

Cabin in Hubbardston

4.94 out of 5 average rating, 157 reviews

Triggers Cabin

Cabin in the woods on a stocked trout pond. Outside deck over the pond for quietly relaxing. Outside fire pit. Gas grill. Inside fireplace.Located in a small private quiet campground. On 200 acres of private wooded land in central Massachusetts. Located on hiking trails that are also used for biking & horseback. Bring your own linens....but kitchen fully equipped. A great place to enjoy the out doors & disconnect & recharge..

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Top guest favorite

Private room in Barre

5 out of 5 average rating, 16 reviews

Dharma House 2

TrishRating, 5 stars3 weeks ago

I chose Dennis’s home to stay while attending a retreat at BCBS and for a night before and after the retreat. It was perfect for my needs—clean, quiet, good WiFi (for work before and after), personalized heating/cooling in bedroom, full kitchen use for before and after, 5 minute drive to BCBS. All as advertised. Even though Dennis was away and I had house to myself, he was very commutative, responsive and as a fellow meditator he is attentive to the needs of those on retreat. Felt very safe at the house, it’s right in heart of the quaint town of Barre. Would definitely stay there again if housing is full at BCBS; also a good option for days before and after time at IMS. Highly recommended.

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 stars2 weeks 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

4.97 out of 5 average rating, 87 reviews

Sunny room with private bathroom

SamRating, 5 stars1 day ago

Yulia and Sacha were the perfect hosts, and made me feel at home. Yulia accommodated my late arrival, the room and bathroom are private, excellent and very clean. The bed was very comfortable, I had an excellent nights sleep and then Yulia unexpectedly made tea the next morning while we chatted. All together a fantastic experience. Highly recommended

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 stars3 weeks 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.

Top guest favorite

A wooden shelf holds an essential oil diffuser, designed with a tree pattern, emitting a gentle green light. Four small bottles of essential oils are neatly arranged next to the diffuser, enhancing the overall aesthetic of the space.

Apartment in Worcester

4.94 out of 5 average rating, 17 reviews

Easy Access Clean Living- Apartment 1R

ChrisRating, 5 stars1 week ago

Place as described. While it is right off an Interstate Bypass, it was still quiet inside. Responsive host. Would book again!

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

An open kitchen area is showcased with modern cabinetry and granite countertops. Two stylish bar stools are positioned at the kitchen island. Natural light streams through large sliding glass doors that lead to an outdoor balcony, enhancing the spacious atmosphere.

Private room in Northborough

4.95 out of 5 average rating, 159 reviews

Swan Home with warm vibes - Guest BR & Pvt Bath

AnithaRating, 5 stars1 week ago

Mena was very nice, the room was spacious and clean and the house was in a beautiful location on the lake. Easy access to the town. Would stay again.

Top guest favorite

A charming two-story yellow house is showcased, featuring black shutters and a welcoming front porch. The porch is adorned with hanging plants and flanked by manicured greenery, creating an inviting entrance set against a well-kept yard.

Private room in Westborough

4.98 out of 5 average rating, 749 reviews

Elegant Rooms in My Antique Home

MattRating, 5 stars4 weeks ago

An awesome place for us to stay after moving to Worcester! Cute and comfortable. Philomena was incredibly responsive and accommodating for our late check-in. Extremely comfortable & private accommodations.

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Vacation rentals in Rutland

Top-rated vacation rentals in Rutland

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Popular amenities for Rutland vacation rentals

Other great vacation rentals in Rutland

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