Plymouth Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Plymouth holiday rentals

Exterior
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Chalet in Plymouth

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is HK$1,568
HK$4,501 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Property grounds
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is HK$1,167
HK$1,455 total
includes taxes & fees
5 Jan - 6 Jan 2026
Treehouse at Wise Pines- NoBo
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Cabin in Grafton

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is HK$1,323
HK$2,849 total
includes taxes & fees
25 Dec - 26 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is HK$1,984
HK$3,163 total
includes taxes & fees
12 Jan - 13 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Terrace/patio
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is HK$973
HK$2,222 total
includes taxes & fees
13 Jan - 14 Jan 2026
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.2 out of 10, Wonderful, (5)
The price is HK$1,167
HK$1,499 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Property grounds
Woodstock Studio | 10 Min to Killington

Apartment in Bridgewater

Woodstock Studio | 10 Min to Killington
10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is HK$1,066
HK$2,060 total
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Studio | 10 Min to Killington
Dining
Whimsical Room & Private Bathroom in Historic Inn

Holiday Home in Chester Depot

Whimsical Room & Private Bathroom in Historic Inn
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is HK$1,004
HK$1,577 total
includes taxes & fees
5 Jan - 6 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn
Fridge, microwave, oven, stovetop
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chalet in Chester

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
10.0 out of 10, Exceptional, (10)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
The price is HK$3,361
HK$5,717 total
includes taxes & fees
25 Dec - 26 Dec
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$918
HK$2,608 total
includes taxes & fees
11 Jan - 12 Jan 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Aerial view
Mountain Green

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (16)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,711
HK$2,296 total
includes taxes & fees
25 Dec - 26 Dec
Mountain Green
Fridge, microwave, oven, stovetop
Chester Farmhouse Ski Retreat near Slopes

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is HK$1,081
HK$2,605 total
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes
Interior
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo in Ludlow

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is HK$832
HK$3,017 total
includes taxes & fees
14 Jan - 15 Jan 2026
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Indoor pool
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Apartment in Killington

Clean & bright condo with mountain views & modern kitchen - walk to lifts
7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
United States
Phillip F.
The price is HK$716
HK$2,331 total
includes taxes & fees
12 Jan - 13 Jan 2026
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Exterior
Killington Ski Resort VT Vacation Condos

Condo in Killington

Killington Ski Resort VT Vacation Condos
3.5 star property
The price is HK$1,509
HK$3,112 total
includes taxes & fees
25 Dec - 26 Dec
Killington Ski Resort VT Vacation Condos
Exterior
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Condo in Killington

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is HK$1,113
HK$2,728 total
includes taxes & fees
8 Jan - 9 Jan 2026
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Property grounds
Gnome Home Mountain Ski Chalet w/Sauna Killington

Chalet in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington
10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is HK$2,183
HK$4,432 total
includes taxes & fees
12 Jan - 13 Jan 2026
Gnome Home Mountain Ski Chalet w/Sauna Killington
3 bedrooms, desk, iron/ironing board, travel cot
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Holiday Home in Bridgewater

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is HK$1,564
HK$4,453 total
includes taxes & fees
13 Jan - 14 Jan 2026
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
TV, fireplace, books
Cozy condo on ski shuttle route with free WiFi & full ktichen

Condo in Killington

Cozy condo on ski shuttle route with free WiFi & full ktichen
8.4 out of 10, Very good, (38)
"Great place. Met our needs. "
United States
Sean K.
The price is HK$910
HK$2,609 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
Property grounds
Comfortable mountain gem with pool, mountain views, & indoor parking space

Condo in Killington

Comfortable mountain gem with pool, mountain views, & indoor parking space
8.4 out of 10, Very good, (32)
"Great stay!"
United States
Bryann F.
The price is HK$941
HK$2,969 total
includes taxes & fees
12 Jan - 13 Jan 2026
Comfortable mountain gem with pool, mountain views, & indoor parking space
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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Top Plymouth Hotel Reviews

Après Inn Killington

Après Inn Killington

10/10 Excellent
"Comfortable, clean, easy to check in. "
Chelsea 1-night trip
Posted 2 days ago
Après Inn Killington

Find out more about Plymouth

Search for holiday rentals in Plymouth on Expedia! You can easily find your home rentals, villas, holiday apartments in Plymouth using one of the methods below:

  • View our selection of featured holiday rentals in Plymouth
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Look no further and take a look at our great range of rental properties in Plymouth!

Frequently asked questions

Can I find a holiday rental in Plymouth?

Yes, there are holiday rentals close to the most popular sights in Plymouth, or you can select a more secluded option if you're looking for a relaxing stay. Plymouth is known for its churches and ski areas.

What are some of the best holiday rentals that Plymouth has to offer?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Plymouth is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Plymouth?

Choose from 45 Expedia holiday rentals in Plymouth for a memorable holiday.

What can I see and do in Plymouth?

Echo Lake and Amherst Lake are a couple of lovely local spots to get outside and enjoy nature. Calvin Coolidge Historic Site and Calvin Coolidge Homestead are other places to visit while you're in town.

What are holiday rentals like in Plymouth?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Plymouth. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.