Holiday rentals in Chittenden

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Top-rated holiday rentals in Chittenden

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

Guest favourite

Home in Rutland

5.0 out of 5 average rating, 120 reviews

ONE ROOM SCHOOL HOUSE

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. It is now a separate, private, room. New European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace/stove for heat and atmosphere. Storage for clothing, skis, snowboards. Exterior bicycle rack. Circular driveway for off-street parking. High speed internet and 65 inch Roku TV with surround sound. Everything brand new. We have added three season screened porch.

22–29 Sep

$316 SGD per night
Guest favourite

Tiny home in Pittsford

4.96 out of 5 average rating, 154 reviews

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

15–22 Jun

$161 SGD per night
Guest favourite

Apartment in Killington

4.95 out of 5 average rating, 124 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

25 Aug – 1 Sep

$134 SGD per night

Popular amenities for Chittenden holiday rentals

Stay near Chittenden's top sights

Mountain Top Inn & Resort32 locals recommend
Baird Farm - Organic Vermont Maple Syrup4 locals recommend
Green Mountain National Golf Course35 locals recommend
Harvest Moon4 locals recommend
Proctor-Pittsford Country Club3 locals recommend
The Canty Trail5 locals recommend

Other great holiday rentals in Chittenden

Superhost

Apartment in Killington

4.84 out of 5 average rating, 341 reviews

Winter is coming! Cute Mountain Getaway!

29 May – 5 Jun

$132 SGD per night
Guest favourite

Home in Middlebury

4.99 out of 5 average rating, 349 reviews

Nice one bedroom cottage

31 Jan – 7 Feb

$180 SGD per night
Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 111 reviews

Mi Casa es su Casa!

19–26 Sep

$156 SGD per night
Guest favourite

Home in Mendon

4.88 out of 5 average rating, 208 reviews

Ranch at Mendon Mt Orchards

15–22 Sep

$250 SGD per night
Guest favourite

Cabin in Chittenden

4.96 out of 5 average rating, 93 reviews

Cabin on The Hill

10–17 Nov

$195 SGD per night
Guest favourite

Cabin in Chittenden

4.98 out of 5 average rating, 89 reviews

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

3–10 Jul

$632 SGD per night
Superhost

Home in Chittenden

4.82 out of 5 average rating, 11 reviews

6 Minute Walk to MT Top Inn 4 BR Pets OK & Grill

2–9 May

$904 SGD per night
Guest favourite

Home in Chittenden

4.9 out of 5 average rating, 81 reviews

Comfortable, relaxing large country home

7–14 Jun

$405 SGD per night
Guest favourite

Home in Chittenden

5.0 out of 5 average rating, 9 reviews

5 minutes to Mt Top Inn - Hiking & Mountain Biking

28 Dec – 4 Jan

$536 SGD per night
Guest favourite

Home in Chittenden

5.0 out of 5 average rating, 45 reviews

Gigi and Pops' Secret Cabin

24 Apr – 1 May

$792 SGD per night
Guest favourite

Home in Rutland

4.87 out of 5 average rating, 75 reviews

Lovely 2-Bedroom on 25 acres

20–27 May

$126 SGD per night
Guest favourite

Flat in Pittsford

4.96 out of 5 average rating, 83 reviews

THE FERN: Relax in peaceful Vermont country

16–23 May

$232 SGD per night

Quick stats about holiday rentals in Chittenden

Total rentals

80 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

3.5K reviews

Nightly prices starting at

$121 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Chittenden