Vacation rentals in Chittenden

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chittenden

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

Guest favorite

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.

Sep 21 – 28

G$49,058 GYD per night
Guest favorite

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.

Jun 2 – 9

G$25,026 GYD per night
Guest favorite

Condo 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

Aug 25 – Sep 1

G$20,858 GYD per night

Popular amenities for Chittenden vacation 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 vacation rentals in Chittenden

Superhost

Condo in Killington

4.84 out of 5 average rating, 341 reviews

Winter is coming! Cute Mountain Getaway!

Jun 5 – 12

G$20,908 GYD per night
Guest favorite

Home in Middlebury

4.99 out of 5 average rating, 349 reviews

Nice one bedroom cottage

Mar 26 – Apr 2

G$27,965 GYD per night
Guest favorite

Home in Leicester

4.98 out of 5 average rating, 129 reviews

Luxurious Cottage Massage Therapy Studio On Site

Feb 16 – 23

G$38,284 GYD per night
Guest favorite

Home in Mendon

4.88 out of 5 average rating, 208 reviews

Ranch at Mendon Mt Orchards

Jul 30 – Aug 6

G$38,652 GYD per night
Guest favorite

Cabin in Chittenden

4.96 out of 5 average rating, 93 reviews

Cabin on The Hill

Nov 10 – 17

G$30,299 GYD per night
Guest favorite

Cabin in Chittenden

4.98 out of 5 average rating, 89 reviews

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

Mar 23 – 30

G$98,073 GYD 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

May 2 – 9

G$140,328 GYD per night
Guest favorite

Home in Chittenden

5.0 out of 5 average rating, 9 reviews

5 minutes to Mt Top Inn - Hiking & Mountain Biking

Dec 28 – Jan 4

G$83,163 GYD per night
Guest favorite

Home in Chittenden

4.9 out of 5 average rating, 81 reviews

Comfortable, relaxing large country home

Aug 4 – 11

G$74,175 GYD per night
Guest favorite

Home in Chittenden

5.0 out of 5 average rating, 45 reviews

Gigi and Pops' Secret Cabin

Apr 23 – 30

G$122,954 GYD per night
Guest favorite

Home in Rutland

4.87 out of 5 average rating, 75 reviews

Lovely 2-Bedroom on 25 acres

May 12 – 19

G$19,554 GYD per night
Guest favorite

Apartment in Pittsford

4.96 out of 5 average rating, 83 reviews

THE FERN: Relax in peaceful Vermont country

Jun 16 – 23

G$36,063 GYD per night

Quick stats about vacation 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

G$18,850 GYD before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Chittenden?

    Four-legged friends are welcome in Chittenden. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do condo rentals in Chittenden have free parking?

    Absolutely! We offer over 10 condo rentals with free parking in Chittenden. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chittenden?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 40 homes with a kitchen, over 40 homes with free parking, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there Chittenden vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chittenden, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Chittenden have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Chittenden. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Chittenden have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in Chittenden. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chittenden?

    Chittenden has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Chittenden?

    Experience the best of Chittenden with our cabin rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chittenden have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Chittenden. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Chittenden?

    Yes! Work meets play with ease at over 30 vacation rentals in Chittenden featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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