Holiday rentals 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.

4.99 out of 5 average rating, 107 reviews

Tiny home in Castleton

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.

4.99 out of 5 average rating, 138 reviews

Flat in Pittsford

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.

4.93 out of 5 average rating, 107 reviews

Apartment in Mendon

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)

4.81 out of 5 average rating, 156 reviews

Home in Rutland

6 Bedroom Home Mendon, VT. (Killington/Pico)

Relax with the whole family or multi families at this peaceful Mountain side retreat in Mendon Vermont. 5 min drive to Pico Ski Resort. 10 min drive to Killington. Great views and sunsets. Driving distance to downtown dinning or apre ski. The House is split into two separate apartments. This is one home but the two apartments are not connected inside and would require access to the other apartment from the Exterior/outside entrance. Great internet WIFi. Speed: Up to 150Mbps Security: WPA2-AES

4.9 out of 5 average rating, 229 reviews

Tiny home in Clarendon

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.

4.9 out of 5 average rating, 907 reviews

Guest house in Granville

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Guest house 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!

5 out of 5 average rating, 137 reviews

Home in Rutland

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.

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.

4.97 out of 5 average rating, 320 reviews

Guest house in Castleton

Bomoseen Bungalow

Located near Lake Bomoseen and Castleton University. This is a charming upstairs apartment in a quiet, residential neighborhood. Walking distance to boat rentals and to a local country store. This apartment provides you with a cozy stay - a bedroom with a queen size bed, sofa bed, and air mattress. There is Roku television, a heat pump for air conditioning or heat, Keurig coffee maker, and more. This is a non smoking unit.

4.96 out of 5 average rating, 609 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Holiday rentals for every style

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Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Rutland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Rutland

4.9 out of 5 average rating, 21 reviews

Home in Mendon

Scenic VT Getaway Lake Days & Mountain Trail Await

ArmandoRating, 5 stars2 months ago

Had an absolutely great stay! Cant say enough great things about it. The house was super clean, was cozy and felt right at home. The home was placed in the perfect location, only 10 minutes from Killington and was very private. It had a nice outdoor area, with a nice creek, an outdoor patio and large outdoor space.

4.97 out of 5 average rating, 58 reviews

Home in Rutland

Mountain Getaway Pet friendly

MelanieRating, 5 stars1 week ago

My sisters and I stayed at Mary’s place in Rutland, VT. Everything about the accommodation was terrific. The home has a nicely designed interior with lovely front and back porch and welcoming yard. Very comfortable sleeping, wonderful bedding and pillows, great showers, super kitchen and great location. Thank you, Mary!

5 out of 5 average rating, 66 reviews

Flat in Wallingford

49 River Street

RaquelRating, 5 stars1 week ago

Immaculate place. Everything you might need! Very charming town. Close to Green Mountain and Appalachian trail hiking. This was our second stay here and we love it. Also, definitely go to Sweet Birch coffee shop while in town. :)

4.86 out of 5 average rating, 92 reviews

Elm Street House

AthenaRating, 5 stars5 days ago

Absolutely lovely stay. The beds were incredibly comfortable, the house was really easy to get around in. Having a washer and dryer made life a lot easier, and it reminded me a lot of the house I grew up in, so I felt right at home!

4.94 out of 5 average rating, 31 reviews

Flat in Killington

Killington ski resort condo

VictorRating, 5 stars1 month ago

i have rented from him for 5 wks plus.. he is always accomodtating and gracious and easy to work with. A delight as always. thanks tom

5 out of 5 average rating, 66 reviews

Farm stay in Clarendon

Dream Catcher Farm

Deborah JRating, 5 stars2 weeks ago

Deanna was a SuperHost as if the word was created for her. I, especially, felt at home. She's delightful, caring and sweet. Deanna's family and her dog Bella are so very welcoming. Bella should be listed as SuperHost #2! Her home is peaceful & beautiful > during the early mornings, there's multitudes of birds which made my Merlin (Bird Identifier) App go wild, including uncommon and rare birds. At night from the deck, viewing white tail deer and a BIG blue heron, and fall asleep with frog murmurs. The location perfectly afforded me several options of my intended adventures (kayaking a different lake each day.) The accommodations and its location, made my daily excursions easy to prepare for each night and leave the day to simply explore and enjoy my day. Location is everything. This was my 2nd time visiting here; and this will be one of MY places to go. CYA in July Deanna!

4.73 out of 5 average rating, 26 reviews

A Hikers Retreat

KylaRating, 5 stars3 months ago

Bernie’s place was perfect for our stay! We booked it for a last minute ski trip to Killington and the location was great. Although we didn’t dine out at all, the place was very close to town with restaurants and shops. It was just two of us so the space was great! Everything was very clean and well stocked. Would definitely stay here again!