Holiday Rentals in Monroe

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Monroe

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is €185
includes taxes & fees
24 Nov - 25 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is €156
includes taxes & fees
23 Nov - 24 Nov
Jiminy Peak Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
TV, fireplace, DVD player, books
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is €217
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Outdoor spa tub
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (211)
"Place was amazing very secluded but close enough to get into town and do things. Our longest drive to go do something was only nine minutes away. Everything was as promised. The only issue we had was the back door entry. The hot tub is right there and when we were standing outside watching nature, we saw bees and wasps going underneath the hot tub. so because we were both chickens, we never went into the hot tub. I probably should’ve called the owner to let him know, but I was a little...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Bear Creek Cabin
Exterior
Bear Creek Cabin
9.8 out of 10, Exceptional, (20)
"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"
The price is €585
includes taxes & fees
25 Nov - 26 Nov
Bear Creek Cabin
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!
Berkshire Lake access
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (44)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (40)
"We stayed at Chris' mansion for my wedding this past weekend and it was everything I expected and more. Although it isn't a full service venue, the owner Chris was sooooo helpful in getting everything we needed for our wedding. He owns a restaurant as well and was able to provide all of our appetizers, servers and bartenders! We even had our rehearsal dinner at his bar down the street called Jax on Tap. The bartenders were absolutely amazing and made us feel so welcome. They even made a sign...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Outdoor spa tub
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.2 out of 10, Very good, (22)
"It was our yearly Guys weekend, everyone had a Great time. The house with every bedroom having a full bath was fantastic you couldn’t ask for more We spent many hours in the indoor pool and the 2 jacuzzi’s we will definitely stay there again"
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (21)
"Good Condo in a great location"
The price is €329
includes taxes & fees
5 Dec - 6 Dec
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (157)
"As good as expected "
Seasons On Mount Snow - Ski-in/Ski-out
Great Place to get away and have clean fresh air surround you!
Exterior
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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.
Don't see what you're looking for?
See all available properties in Monroe
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Monroe you may be interested in

Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1043)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is €123
includes taxes & fees
11 Dec - 12 Dec
Hotel Downstreet
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is €185
includes taxes & fees
24 Nov - 25 Nov
Vacation Village in the Berkshires
Mountaineer Inn
Fireplace
Mountaineer Inn
2.0 star property
9.2 out of 10, Wonderful, (349)
"Nice quiet getaway about 30 min from Stratton. We went off season to see the leaves in October so a lot of stores and restaurants were closed, but what is open nearby is delicious. The place is a standard motel, room was clean, coffee maker in the dining area, several lounge spaces, pool table, and a fire pit. Nice ski decor. Sauna, hot tub, and pool spaces were closed. Check in/check out super easy. Easy to reach staff, I’d return next time I plan on coming up here. "
Mountaineer Inn
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.

Frequently asked questions

Are there holiday rentals in Monroe?

Yes, there are holiday rentals close to the most popular sights in Monroe, or you can select a more secluded option if you're looking for a relaxing stay.

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

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Monroe is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

What’s there to see and do in Monroe?

Green Mountain National Forest and Deerfield River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Monroe State Forest and Monroe Town Hall.

What’s a holiday rental in Monroe like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monroe. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.