---
title: "Pittsfield Vacation Rentals from $263: Search Short-Term Rentals | Expedia.com"
description: "Find the best deals on Pittsfield vacation rentals with Expedia.com. We offer a huge selection of top vacation homes for rental in Vermont. Book your next vacation with us!"
canonical: "https://www.expedia.com/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-14T09:54:26Z
---

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- [Pittsfield Travel Guide](https://www.expedia.com/Pittsfield.dx184066)
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- [Flights to Pittsfield](https://www.expedia.com/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)
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- [Pittsfield Vacation Packages](https://www.expedia.com/Pittsfield.d184066.Destination-Travel-Guides)

# Pittsfield Vacation Rentals
![A lake surrounded by autumn-colored trees and a rocky shoreline.](https://images.trvl-media.com/place/184066/3bf9267c-5fee-4448-a4ae-c2b3d3078b93.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

[Check prices for these dates, December 14 – 15, 2026](https://www.expedia.com/Hotel-Search?regionId=184066&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&sort=VACATION%5FRENTAL)

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## Our top choices for Pittsfield vacation rentals

### [1\. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont](https://www.expedia.com/Pittsfield-Hotels-Peak-Hill-3-Bedroom.h109476281.Hotel-Information)

![An outdoor deck with a fire pit and wicker furniture.](https://images.trvl-media.com/lodging/110000000/109480000/109476300/109476281/0c919bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: North Sherburne
- Guest rating: 10/10 (Exceptional, 1 review)
- Price: $542 nightly, $702 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: "Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this..., by Essa R.

### [2\. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking](https://www.expedia.com/Pittsfield-Hotels-NEW-Smart-3BR-Basecamp-W-Hot-Tub.h123480177.Hotel-Information)

![A spacious kitchen with wooden cabinets, a dining area with a red and white table, and a cozy seating area with a red sofa.](https://images.trvl-media.com/lodging/124000000/123490000/123480200/123480177/b4360759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Sherburne
- Guest rating: 10/10 (Exceptional, 2 reviews)
- Price: $577 nightly, $747 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: "On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we..., by Heidi P.

### [3\. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you](https://www.expedia.com/Chittenden-Hotels-Delightful-2-Bedroom.h138065635.Hotel-Information)

![A wooden staircase leading to a loft bedroom with a bed, a fireplace, and a kitchen area.](https://images.trvl-media.com/lodging/139000000/138070000/138065700/138065635/5c778a7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chittenden
- Price: $319 nightly, $357 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals

### [4\. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings](https://www.expedia.com/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information)

![An outdoor deck with a grill, white plastic chairs, and a glass table.](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/11024da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Sherburne
- Guest rating: 8/10 (Very good, 17 reviews)
- Price: $468 nightly, $528 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: We had a great time!, by Matthew R.

### [5\. Gnome Home Mountain Ski Chalet w/Sauna Killington](https://www.expedia.com/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information)

![A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/48be0320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Stockbridge
- Guest rating: 10/10 (Exceptional, 7 reviews)
- Price: $451 nightly, $475 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!, by Gerald S.

### [6\. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531](https://www.expedia.com/Killington-Hotels-The-Suites-Next-Door-Studio-Room-At-Killington-Resort-On-The-Bus-Route-DISCOUNTED-LIFT-TICKETS.h102479791.Hotel-Information)

![A backyard with a swimming pool, white deck chairs, and a green umbrella.](https://images.trvl-media.com/lodging/103000000/102480000/102479800/102479791/5c08aa6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.6/10 (Exceptional, 5 reviews)
- Price: $263 nightly, $340 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Place was great, by Nathan H.

### [7\. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.](https://www.expedia.com/Killington-Hotels-Killington-Center-Renovated-Studio-With-Kitchenette-On-Bus-Route-And-Discounted-Ski-Rentals.h123022185.Hotel-Information)

![Wide steps and a handrail lead into the water from the deck.](https://images.trvl-media.com/lodging/124000000/123030000/123022200/123022185/986b91f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.4/10 (Exceptional, 10 reviews)
- Price: $253 nightly, $327 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . , by Asad B.

### [8\. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington](https://www.expedia.com/Killington-Hotels-Tranquil-Peaks-Studio-At-Killington-Center-Perfect-For-A-Getaway-In-The-Heart-Of-Killington.h110285457.Hotel-Information)

![Take a swim or choose a lounger beside the shared outdoor pool when it is open.](https://images.trvl-media.com/lodging/111000000/110290000/110285500/110285457/cf20a549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.6/10 (Exceptional, 5 reviews)
- Price: $263 nightly, $340 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Great room!, by Carla M.

### [9\. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.](https://www.expedia.com/Killington-Hotels-Picos-Doorstep-Ski-OnOff.h110405218.Hotel-Information)

![A multi-story building with a snow-covered roof and a parking area in front.](https://images.trvl-media.com/lodging/111000000/110410000/110405300/110405218/8dafb292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.8/10 (Exceptional, 14 reviews)
- Price: $296 nightly, $384 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! , by Susanne B.

### [10\. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631](https://www.expedia.com/Killington-Hotels-Ski-Condo-Close-To-Killington-Discounted-Lift-Tickets-And-Shuttle-Bus-Killington-Center-631.h110145970.Hotel-Information)

![The community pool has entry steps and handrails, with seating around the deck.](https://images.trvl-media.com/lodging/111000000/110150000/110146000/110145970/d897c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9/10 (Wonderful, 7 reviews)
- Price: $252 nightly, $327 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication., by Marcus G.

### [11\. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6\. Discounted Ski Rentals.](https://www.expedia.com/Killington-Hotels-The-Swirl-Suite-At-Killington-Renovated-2RM2BA-Suite-Sleeps-6-Discounted-Lift-Tickets.h111231486.Hotel-Information)

![Enjoy the shared outdoor pool during its operating season, with loungers around the deck.](https://images.trvl-media.com/lodging/112000000/111240000/111231500/111231486/0a5417c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.2/10 (Wonderful, 10 reviews)
- Price: $375 nightly, $486 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10\. Highly recommend., by Lisa

### [12\. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332](https://www.expedia.com/Killington-Hotels-Skiers-Suite-2RM2BA-Renovated-Condo-On-The-Bus-Route-W-Pool-Discounted-Lift-Tickets-332.h104949519.Hotel-Information)

![A modern kitchen with a large island, wooden cabinets, and a red stool. There is a dining area with a wooden table and chairs, and a red telephone booth.](https://images.trvl-media.com/lodging/105000000/104950000/104949600/104949519/aa4528cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.4/10 (Exceptional, 12 reviews)
- Price: $398 nightly, $515 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Quick trip but would stay here again, by John O.

### [13\. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532](https://www.expedia.com/Killington-Hotels-Sweet-Suite-Modern.h34011431.Hotel-Information)

![A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.](https://images.trvl-media.com/lodging/35000000/34020000/34011500/34011431/aff50605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 9.6/10 (Exceptional, 73 reviews)
- Price: $374 nightly, $486 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: overall it is good stay for a vacation, by Michael S.

### [14\. Jack S\`Bearo - Slopes, Fireplace, Pool](https://www.expedia.com/Killington-Hotels-Jack-SBearo-Slopeside-At-Pico-Shuttle-To-Killy.h101900661.Hotel-Information)

![A fireplace with a stone facade, a fire burning inside, and a log holder filled with logs.](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900661/58db806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 10/10 (Exceptional, 17 reviews)
- Price: $234 nightly, $264 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Great condo and building. Everything in excellent condition. Convenient location., by Joseph S.

### [15\. CubsCorner - Pool, Sauna, Gym, Close to Mountain!](https://www.expedia.com/Killington-Hotels-CubsCorner-Large-1BR.h101900654.Hotel-Information)

![A modern living room with a fireplace, a grey sofa, and a kitchen area with dark cabinets and a white countertop.](https://images.trvl-media.com/lodging/102000000/101910000/101900700/101900654/dbbe4b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: $484 nightly, $535 total, Nov 25 - Nov 26, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Great location with access to both Pico and Killington Mountains!, by Olaf G.

### [16\. 4BR Killington Home Perfect for Families, Pet-Friendly](https://www.expedia.com/Killington-Hotels-4BR-Killington-Home-Perfect-For-Families.h120663187.Hotel-Information)

![A wooden deck with a railing, surrounded by trees and a building with a staircase.](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663187/d8e327f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Sherburne
- Guest rating: 10/10 (Exceptional, 24 reviews)
- Price: $627 nightly, $812 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. , by Christina V.

### [17\. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.](https://www.expedia.com/Rutland-Hotels-The-Mendon-Cottage-Charming-Home-Close-To-Killington-Discounted-Lift-Tickets.h107908933.Hotel-Information)

![A wooden deck with a lattice railing overlooking a dense forest.](https://images.trvl-media.com/lodging/108000000/107910000/107909000/107908933/dff129d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Mendon
- Guest rating: 9.6/10 (Exceptional, 24 reviews)
- Price: $402 nightly, $521 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’., by Diane

### [18\. The Suites at Killington Center](https://www.expedia.com/Killington-Hotels-The-Suites-At-Killington-Center.h121193871.Hotel-Information)

![A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, and a white fence.](https://images.trvl-media.com/lodging/122000000/121200000/121193900/121193871/88ef042b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Price: $427 nightly, $470 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals

### [19\. Mountain Green ground-floor condo with private yard off the patio](https://www.expedia.com/Killington-Hotels-Welcoming-Condo-Near-The-Slopes-With-Free-WiFi-And-Full-Kitchen.h131748085.Hotel-Information)

![A rectangular swimming pool with a covered seating area and a small building, surrounded by trees with autumn foliage.](https://images.trvl-media.com/lodging/132000000/131750000/131748100/131748085/248feb96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Price: $260 nightly, $294 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals

### [20\. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift](https://www.expedia.com/Killington-Hotels-Trailside-Loft-At-Pico-Ski-InOut-Condo-W-Loft-2BR-Steps-To-Lift.h120120957.Hotel-Information)

![Pass snacks across the counter without leaving the conversation in the main room.](https://images.trvl-media.com/lodging/121000000/120130000/120121000/120120957/8e128d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Guest rating: 10/10 (Exceptional, 3 reviews)
- Price: $533 nightly, $691 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Pittsfield vacation rentals
- Review: Great midweek ski vacation. Easily walked to the slope to get to the kiosk for our ticket. Kitchen had all that we needed. , by Casey C.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Find vacation rentals that suit your style

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[Condos](https://www.expedia.com/Hotel-Search?destination=Pittsfield,%20Vermont,%20United%20States%20of%20America&regionId=184066&latLong=43.772289,-72.812881&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=CONDO)

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[Villas](https://www.expedia.com/Hotel-Search?destination=Pittsfield,%20Vermont,%20United%20States%20of%20America&regionId=184066&latLong=43.772289,-72.812881&adults=2&startDate=2026-11-21&d1=2026-11-21&endDate=2026-11-23&d2=2026-11-23&lodging=VILLA)

## Top Pittsfield Hotel Reviews

### [Mountain Meadows Lodge](https://www.expedia.com/Killington-Hotels-Mountain-Meadows-Lodge.h894095.Hotel-Information)

![A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.](https://images.trvl-media.com/lodging/1000000/900000/894100/894095/f3f84aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: Nice place. Close to the mountain. Nice aesthetic quaint and homey feel but also clean new and well kept. Hotel restaurant is a bit mediocre but not too bad. Good service so far on my trip too., by Timothy, February 3, 2024, rated 10/10 Excellent

### [The Trailside Inn](https://www.expedia.com/Killington-Hotels-The-Trailside-Inn.h8370321.Hotel-Information)

![A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/3a9d5306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Sherburne
- Review: I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic. We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by. It was very cold Saturday so we didn't stay long at the mountain. When we..., by Alyssa, March 7, 2017, rated 10/10 Excellent

### [Greenbrier Inn](https://www.expedia.com/Killington-Hotels-Greenbrier-Inn.h1176792.Hotel-Information)

![A spacious loft-style living area with a high ceiling, wooden beams, and a cozy fireplace. A staircase with a wooden railing leads to an upper level.](https://images.trvl-media.com/lodging/2000000/1180000/1176800/1176792/7deb28f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: The breakfast was very nice with a large assortment of fruit, breads, muffins, cereal, cheese, yogurts., by KEVIN, October 30, 2024, rated 10/10 Excellent

### [Mountain Sports Inn](https://www.expedia.com/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information)

![A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: Enjoyed my late season short stay here. Nice to have a tuning room with a platform. Close to K-1, closer to Ramshead and Snowshed. Right next to Rivershed restaurant which was nice. Late check in was easy. Bed was surprisingly comfortable. Continental breakfast is what you’d expect. All told, will come back if the price is right., by Julianne, April 13, 2025, rated 10/10 Excellent

### [Snowed Inn](https://www.expedia.com/Killington-Hotels-Snowed-Inn.h1153997.Hotel-Information)

![A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.](https://images.trvl-media.com/lodging/2000000/1160000/1154000/1153997/4776fd2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: We got in late because we had an issue charging our electric car. The guy was so friendly and even ran an extension cord so we could charge our car. The room was clean and so rustic I loved it. The jetted tub was amazing and relaxing. Lastly the breakfast was delicious and we were told made from scratch! It was so good Definitely would stay there again!, by Tammy, June 5, 2022, rated 10/10 Excellent

### [Après Inn Killington](https://www.expedia.com/Killington-Hotels-Apres-Inn-Killington.h104893073.Hotel-Information)

![A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.](https://images.trvl-media.com/lodging/105000000/104900000/104893100/104893073/ae40488d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: I had been following the renovations of this hotel on social media. When I recently came through VT to Drop my child off at summer camp, I decided to give Apres Inn a try. Everything was very clean, very comfortable, check-in was a breeze. Definitely will be back on subsequent trips., by Anonymous traveler, June 22, 2024, rated 10/10 Excellent

### [The Mountain Inn at Killington](https://www.expedia.com/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information)

![A building with a modern design, featuring large windows and a covered outdoor seating area.](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: ski trip, great location, by Donna, March 22, 2025, rated 10/10 Excellent

### [The Mountain Top Inn & Resort](https://www.expedia.com/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information)

![A spacious room with large windows, a stone wall, and a wooden ceiling.](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chittenden
- Review: We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!, by Anonymous traveler, August 15, 2015, rated 10/10 Excellent

### [North Star Lodge and Resort](https://www.expedia.com/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information)

![A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/2b6f6a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Killington
- Review: The staff made check in a breeze. The king room is large, clean and comfortable. The extra convenience is the restaurant right next door!, by Thayer, June 21, 2025, rated 10/10 Excellent

### [The Jackson](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

![A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: West Woodstock
- Review: Fantastic bed and breakfast tucked away from all the hustle., by Tiffany, December 1, 2024, rated 10/10 Excellent

### [Sleep Woodstock Motel](https://www.expedia.com/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information)

![A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/3536a275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Woodstock
- Review: We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room..., by John, July 8, 2024, rated 10/10 Excellent

### [On The River Inn](https://www.expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![Two Adirondack chairs by a river with a forested hillside in the background.](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/6a840315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: West Woodstock
- Review: The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10\. I will definitely go back again., by Ayleen, February 12, 2024, rated 10/10 Excellent

### [Green Trails Inn](https://www.expedia.com/Brookfield-Hotels-Green-Trails-Inn.h127144120.Hotel-Information)

![A two-story building with a porch, outdoor seating, and flags.](https://images.trvl-media.com/lodging/128000000/127150000/127144200/127144120/72efb27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brookfield
- Review: Staying there was like traveling on time and we were avle to learn about the history of the original house and famous bridge in front. The room was extremely clean, comfortable and cozy. The staff very responsive and kind. Breakfast served was delicious and fresh., by Jesus, October 22, 2026, rated 10/10 Excellent

### [Brandon Inn](https://www.expedia.com/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information)

![A snow-covered building with a sign reading "BRAMPTON INN".](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brandon
- Review: Nice and clean place. Staff were very friendly., by Shahram, July 7, 2024, rated 10/10 Excellent

### [Inn at Neshobe River](https://www.expedia.com/Brandon-Hotels-Inn-At-Neshobe-River.h1581667.Hotel-Information)

![A two-story house with a porch, surrounded by trees.](https://images.trvl-media.com/lodging/2000000/1590000/1581700/1581667/354bde1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Brandon
- Review: Owners were very nice. The room and bathroom were very clean. Beautiful area of Vermont. Felt very safe staying here. Would recommend., by Anonymous traveler, August 24, 2015, rated 10/10 Excellent

### [Hampton Inn Rutland](https://www.expedia.com/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information)

![A covered outdoor area with a wooden ceiling, potted plants, and a bench.](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/a61b527d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Rutland
- Review: Mike at the front desk was phenomenal! So helpful, friendly, and funny. We accidentally left a dress hanging in the closet of our room and he sent it to us with no problem. He was really great!, by Anonymous traveler, August 11, 2021, rated 10/10 Excellent

### [Best Western Inn & Suites Rutland-Killington](https://www.expedia.com/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information)

![A modern room with a glass door leading to a patio, two wicker chairs, a small table, and a wooden ceiling beam.](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9ecaf644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Rutland
- Review: Friendly,accommodating, by Judie, October 7, 2024, rated 10/10 Excellent

### [Lincoln Inn & Gallery](https://www.expedia.com/Woodstock-Hotels-Lincoln-Inn-Gallery.h113896234.Hotel-Information)

![A large, white, two-story house with a symmetrical facade, surrounded by a well-maintained lawn and tall trees.](https://images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/e574044a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Woodstock
- Review: We had a wonderful stay at the Lincoln Inn. The property was very cute and historic, and the innkeeper was warm and welcoming., by Jennifer, March 24, 2025, rated 10/10 Excellent

## Find out more about Pittsfield

### Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

### Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $263 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

### How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Frequently Asked Questions

### Can I find a vacation rental in Pittsfield?

Yes, there are vacation rentals close to popular sights in Pittsfield, or you can choose a more remote option if you're looking for relaxation. Pittsfield is known for its bars and restaurants.

### What are some of the best vacation rentals that Pittsfield has to offer?

[PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.](https://www.expedia.com/Woodstock-Hotels-PRIVATE-AFFORDABLE-Charming-Custom-Ranch-In-S-Woodstock-WIFI-And-AC.h33961408.Hotel-Information): This vacation home rental outside Pittsfield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

### How many vacation rentals are there in Pittsfield?

Expedia has 28 vacation rentals for your stay in Pittsfield.

### What can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Pittsfield Town Hall and Roger Clark Memorial Central Library are other places to visit while you're in town.

### What are vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

## Explore a world of travel with Expedia

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- [Hartland Vacation Rentals](https://www.expedia.com/Hartland-Vacation-Rentals.d6052375.Travel-Guide-VacationRentals)
- [Brookfield Vacation Rentals](https://www.expedia.com/Brookfield-Vacation-Rentals.d184041.Travel-Guide-VacationRentals)

## Other language versions

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