
Holiday rentals in Rutland
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Top-rated holiday rentals in Rutland
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My house is your house!
Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Home Sweet Home
Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Cozy Contemporary Downtown Texaco
Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Apartment in Vermont Historic Home
This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

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.

Dog heavenly! Private, beautiful and relaxing.
Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

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!

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.

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.

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.

Cozy Poultney Village Apartment
I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Elegant Alpine Condo
Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718
Popular amenities for Rutland holiday rentals
Other great holiday rentals in Rutland

Winter is upon us!

Cozy Rutland Retreat

The Gourmet Roost

Scenic Vermont Green Mountain Retreat

Cozy One-Bedroom Retreat with Mountain Views

Spacious Ski Chalet Near Killington w/ Pool Table

Kingsley Homestead

*Pet Friendly* The Madden Mountain Home
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 166 | € 165 | € 154 | € 131 | € 136 | € 128 | € 129 | € 129 | € 133 | € 141 | € 138 | € 157 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Rutland?
Four-legged friends are welcome in Rutland. Choose from more than 40 vacation rentals for guests traveling with pets.
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.
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.
Do house rentals in Rutland have wifi?
Absolutely! We offer over 50 house rentals with wifi in Rutland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Rutland?
Experience the best of Rutland with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Rutland?
Rutland has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Rutland

Total holiday rentals
Explore 120 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 6,230 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
120 of Rutland holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Rutland rentals

4.9 Average rating
Rutland stays are highly rated by guests – averaging 4.9 out of 5!
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- Stratton Mountain
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- Sugarbush Resort
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