Photo by George Sykes

Plymouth Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Plymouth vacation rentals

Beach
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.
$486 nightly
The price is $544
Dec 16 - Dec 17
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Property grounds
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

Vacation Home in Plymouth

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
2.0 star property
$544 nightly
The price is $609
Dec 15 - Dec 16
Total with taxes and fees
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
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
$319 nightly
The price is $357
Dec 15 - Dec 16
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds
Treehouse at Wise Pines- SoBo

Cabin in Woodstock

Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
$171 nightly
The price is $187
Dec 16 - Dec 17
Total with taxes and fees
Treehouse at Wise Pines- SoBo
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, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$330 nightly
The price is $361
Dec 14 - Dec 15
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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.
$255 nightly
The price is $288
Dec 16 - Dec 17
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Fridge, microwave, oven, stovetop
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cottage in Mendon

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
$367 nightly
The price is $411
Dec 15 - Dec 16
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Cottage in Ludlow

Ludlow Ski Cabin 2 Mi to Ski Parking
3.0 star property
$333 nightly
The price is $366
Dec 14 - Dec 15
Total with taxes and fees
Ludlow Ski Cabin 2 Mi to Ski Parking
Condo, 2 Bedrooms | Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

Condo in The Woods

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
$566 nightly
The price is $631
Dec 15 - Dec 16
Total with taxes and fees
The Woods by Killington Vacation Rentals - 2 Bedrooms
Indoor pool, a heated pool
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Condo in The Woods

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
2.0 star property
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
$401 nightly
The price is $453
Dec 15 - Dec 16
Total with taxes and fees
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Cabin in Killington

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
$449 nightly
The price is $507
Dec 15 - Dec 16
Total with taxes and fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

Condo in Killington

The Suites at Killington Center
3.5 star property
$340 nightly
The price is $374
Dec 15 - Dec 16
Total with taxes and fees
The Suites at Killington Center
TV, DVD player, books
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.
$252 nightly
The price is $285
Dec 15 - Dec 16
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
1 bedroom, free WiFi, bed sheets
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
9.4 out of 10, Exceptional, (3)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
$172 nightly
The price is $193
Dec 14 - Dec 15
Total with taxes and fees
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Internet, bed sheets
Efficient condo near slopes with kitchenette & great location

Apartment in Ludlow

Efficient condo near slopes with kitchenette & great location
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
$200 nightly
The price is $226
Dec 17 - Dec 18
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Restaurant
Mountain Green Resort

Apartment in Killington

Mountain Green Resort
4.0 star property
$553 nightly
The price is $609
Dec 15 - Dec 16
Total with taxes and fees
Mountain Green Resort
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Condo in Killington

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$256 nightly
The price is $289
Dec 15 - Dec 16
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Exterior detail
Ben & Jerry Suite | Skiing | Hiking | Biking

Apartment in Bridgewater

Ben & Jerry Suite | Skiing | Hiking | Biking
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
$215 nightly
The price is $235
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ben & Jerry Suite | Skiing | Hiking | Biking
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in Ludlow

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$269 nightly
The price is $292
Dec 15 - Dec 16
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Fridge, microwave, oven, stovetop
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
$298 nightly
The price is $337
Dec 16 - Dec 17
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Plymouth Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Overall good experience."
valerie 1-night trip
Posted 1 day ago
Hampton Inn Rutland

Find out more about Plymouth

Everything you need to know about Plymouth 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 Plymouth 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 Plymouth vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Plymouth vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Plymouth. 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 Plymouth 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 $193 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 Plymouth rentals

At Expedia, we put the best Plymouth 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 Plymouth 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 Plymouth 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 Plymouth. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Plymouth?

Yes, we have vacation rentals close to top sights in Plymouth, or you can select a more secluded option if you're looking for relaxation. Plymouth is known for its churches and ski areas.

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

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home near Plymouth is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Plymouth?

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

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 vacation rentals like in Plymouth?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Plymouth. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for small groups.