Are there vacation rentals with a dedicated workspace in Rutland?

Yes! Work meets play with ease at over 60 vacation rentals in Rutland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Are there pet-friendly vacation rentals in Rutland?

Four-legged friends are welcome in Rutland. Choose from more than 30 vacation rentals for guests traveling with pets.

How much does it cost to stay in apartment rentals in Rutland?

Experience the best of Rutland with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do apartment rentals in Rutland have wireless internet?

Absolutely! We offer over 50 apartment rentals with wireless internet in Rutland. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Rutland?

Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wireless internet, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Do house rentals in Rutland have air conditioning?

Absolutely! We offer over 40 house rentals with air conditioning in Rutland. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Rutland

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Rutland

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

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Superhost

A functional kitchen features a central wooden island with seating for two on green stools. White cabinetry complements stainless steel appliances, including a stove and microwave. Modern flooring enhances the spacious layout, which is equipped with essential storage and preparation areas.

Apartment in Rutland

4.85 out of 5 average rating, 232 reviews

Home Sweet Grove Street

Enormous 4 bedroom/1 bathroom apartment. 2000 sq ft.. Second floor. Entrance in front of the house. Parking in rear. Large dining room, living room and kitchen. Covered porch off of kitchen to enjoy some time outside. Tons of natural light. Perfect for large families or groups of friends. Dining room table seats 10+. House is one block from downtown. Walk to the restaurants, bars, movie theater, grocery store, bus depot, train depot,Walmart. Convenience store 3 houses down. Skiing 20 mins away.

Top guest favorite

Two white chairs are positioned on a moss-covered area beside a flowing stream. Sunlight softly filters through the surrounding trees, highlighting the natural greens of the landscape. The sound of rushing water is present, contributing to the tranquil atmosphere.

Tiny home in Castleton

4.99 out of 5 average rating, 107 reviews

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Top guest favorite

Two red adirondack chairs are positioned on a grassy area overlooking a calm pond. The water reflects a tree-lined shoreline under a partially cloudy sky. A wooden dock extends into the water, enhancing the tranquil outdoor setting.

Apartment in Pittsford

4.99 out of 5 average rating, 138 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or young children.

Guest favorite

A close-up of a modern keypad lock is displayed, featuring numeric buttons and a lever handle. The lock is mounted on a wooden door, showcasing the wood grain texture.

Condo in Mendon

4.93 out of 5 average rating, 107 reviews

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

Guest favorite

A set of glass doors opens to a spacious outdoor area featuring a stone fire pit surrounded by blue chairs. Lush greenery forms the background, enhancing the tranquil setting. Natural light streams in, highlighting the inviting atmosphere of the space.

Tiny home in Clarendon

4.9 out of 5 average rating, 230 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favorite

Home in Rutland

4.89 out of 5 average rating, 190 reviews

Killington/Okemo, Spacious, 7p Hot tub, Mtn.views!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mountain views, peaceful brook on 1+ acre property. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV.

Top guest favorite

The exterior of a historic guesthouse is shown, featuring white siding and classic black shutters. The structure is located amidst lush green grass and trees, with a red barn visible in the background. A gentle sunset casts a warm glow over the scene.

Guesthouse in Wallingford

4.98 out of 5 average rating, 697 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Guest favorite

Cabin in West Rutland

4.88 out of 5 average rating, 177 reviews

VT MOUNTAIN LOG CABIN, CLOSE TO KILLINGTON/PICO

REAL VERMONT LOG CABIN ON MOUNTAIN, W/ PINE WOOD WALLS & FURNISHINGS. 16 MILES TO PICO SKI RESORT, JUST A LITTLE FARTHER TO KILLINGTON. PRIVATE SETTING W/ 2 BEDROOMS, 2 FULL BATHS. 1 QUEEN BED, 1 DOUBLE & SINGLE BUNK BED, COUCH AND AIR BED THAT LOOKS/FEELS LIKE A REGULAR BED. HOUSE SLEEPS 6. FIRE PIT & GRILL. GREAT IN FALL FOR LEAF PEEPING. CLOSE TO DINING, MOVIES, SKATING & STORES IN RUTLAND. SEE CHECK IN INSTRUCTIONS FOR CABIN INFO. PLS COMPLETE 1 PAGE CONTRACT PRIOR TO ARRIVAL.

Top guest favorite

A shaded porch offers a comfortable seating area with a maroon couch and a round rug on dark wooden flooring. White lattice railings create an open view of the grassy front yard and tree-lined street. The neighborhood features houses and greenery, contributing to a peaceful atmosphere.

Home in Poultney

4.92 out of 5 average rating, 123 reviews

Cozy Home in Poultney, Vermont.

If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

Guest favorite

Home in Clarendon

4.96 out of 5 average rating, 296 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Top guest favorite

A charming white schoolhouse is surrounded by a blanket of fresh snow, with snow-covered bushes outlining the property. A tree stands bare nearby, while an American flag is displayed on the facade. The scene conveys a serene winter atmosphere in a quiet setting.

Home in Rutland

5 out of 5 average rating, 138 reviews

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

Guest favorite

A bathroom vanity showcases a marble countertop with a wash basin. Elegant chrome fixtures are paired with a decorative pink and teal backsplash. A clear soap dispenser labeled 'HAND SOAP' and a pastel-colored decorative jar filled with cotton balls add a touch of color.

Apartment in Rutland

4.86 out of 5 average rating, 184 reviews

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Rutland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Rutland

Guest favorite

A wooden guest book prominently displays the name 'The Maple Leaf Inn' along with an illustration of the inn, surrounded by trees. The book rests on a polished wooden table, with warm tones highlighting its rustic appeal.

Home in Mendon

4.9 out of 5 average rating, 21 reviews

Scenic VT Getaway Lake Days & Mountain Trail Await

Top guest favorite

A well-appointed bathroom is featured, showcasing a modern shower enclosed in black framing. Marble flooring complements the wood vanity with gold fixtures. Rich green walls and elegant wainscoting add depth, while framed artwork enhances the overall aesthetic.

Home in Rutland

4.97 out of 5 average rating, 58 reviews

Mountain Getaway Pet friendly

Superhost

A display of fresh produce is arranged in wooden crates. Onions, with their golden skins, are piled in the foreground. Basil is presented in a blue container, while various colorful vegetables, including tomatoes and greens, are visible in the background.

Apartment in Rutland

4.76 out of 5 average rating, 63 reviews

Comfortable In Town Apartment

Guest favorite

A welcoming dining area is showcased with a light-colored table set at the center. Surrounding windows, adorned with floral curtains, allow natural light to fill the space. Decorative accents, such as wooden furniture and artwork, contribute to a charming atmosphere.

Apartment in Rutland

4.86 out of 5 average rating, 92 reviews

Elm Street House

Top guest favorite

A clear, inviting swimming pool occupies a spacious area with sunlit turquoise water. Surrounding the pool is a textured stone patio, leading to lush green grass and trees in the background, enhancing the outdoor setting.

Farm stay in Clarendon

5 out of 5 average rating, 66 reviews

Dream Catcher Farm

Top guest favorite

A wooden-paneled bathroom features a round sink with modern fixtures and a wall-mounted mirror reflecting a floral design. Soft lighting is provided by two sconces, while a towel hangs neatly on a rack. A small decorative lamp adds a cozy touch beside the sink.

Home in Proctor

5 out of 5 average rating, 10 reviews

Adorable townhouse in Proctor

Superhost

Apartment in Rutland

4.73 out of 5 average rating, 26 reviews

A Hikers Retreat

Guest favorite

A functional laundry area is equipped with a stacked washer and dryer, positioned beside a compact vanity with a sink. Natural light filters in from a window, illuminating the space. A cozy living area is visible through the open door, featuring a sofa and a light rug.

Apartment in Clarendon

5 out of 5 average rating, 21 reviews

Cozy One-Bedroom Retreat with Mountain Views

Show all

Quick stats about vacation rentals in Rutland

Total rentals
120 properties
Total number of reviews
6.2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
120 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Rutland?
Yes! Work meets play with ease at over 60 vacation rentals in Rutland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Rutland?
Four-legged friends are welcome in Rutland. Choose from more than 30 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Rutland?
Experience the best of Rutland with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Rutland have wireless internet?
Absolutely! We offer over 50 apartment rentals with wireless internet in Rutland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Rutland?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wireless internet, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Rutland have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Rutland. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Rutland

Top-rated vacation rentals in Rutland

Vacation rentals for every style

Popular amenities for Rutland vacation rentals

Other great vacation rentals in Rutland

Quick stats about vacation rentals in Rutland

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

Destinations to explore