Windsor Vacation Rentals from AED 412: Search Short-Term Rentals

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Our top choices for Windsor vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Robert

AED 412 total

includes taxes & fees

1 Oct - 2 Oct

2. Vacation Village in the Berkshires

Williamstown

Alex

AED 437 total

includes taxes & fees

1 Sep - 2 Sep

3. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Gerard C.

AED 1,905 total

includes taxes & fees

1 Sep - 2 Sep

Coffee/tea maker, fridge, microwave, oven

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Megan A.

AED 1,571 total

includes taxes & fees

19 Sep - 20 Sep

5. Huttopia Berkshires

Williamstown

GEORGINA

AED 399 total

includes taxes & fees

8 Sep - 9 Sep

6. Penthouse Apartment on Park Street

Adams

Margaret C.

AED 1,034 total

includes taxes & fees

13 Sep - 14 Sep

7. Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Noah K.

AED 3,418 total

includes taxes & fees

6 Sep - 7 Sep

8. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Jamie M.

AED 1,522 total

includes taxes & fees

1 Sep - 2 Sep

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"STOP your search now. Vacation Village is THE place to stay if you're visiting the Berkshires, any time of year. The staff are all absolutely wonderful and dedicated to making sure all guests are 100% satisfied. Brad, the manager is kind and incredibly efficient, always on top of things. The rooms, are all spacious, and the porch/balcony are great and really set the property apart from others. Beds, Couches, linens, all comfortable, kitchen well stocked, parking is always a breeze. Pools are always clean, grounds clean and well maintained. I wouldnt stay anywhere else. It definitely feels like a village 😄Easy access to fun and necessities. Dont forget to hop over the line into New York, its worth a slow morning drive."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Quality Inn Lee - Lenox South

8/10 Good

"Very nice and clean motel...better than I thought it would be, so we felt a lot better about staying there. We were a bit disappointed about the breakfast portion of the day so went out for brunch instead. The breakfast sandwiches weren't that great and not many tables to sit at. But overall, the rooms and bathrooms were very clean and modern."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, there are vacation rentals close to well known attractions in Windsor, or you can select a more secluded option if you'd like a relaxing place to stay. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Windsor is located near skiing 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. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Wahconah Falls State Park. Mount Greylock State Reservation Visitor Center and Pontoosuc Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Windsor. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.

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Check prices for these dates

Our top choices for Windsor vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

5. Huttopia Berkshires

6. Penthouse Apartment on Park Street

7. Riverbend Berkshire East Basecamp - 3 bedrooms available

8. Charming, updated 3 bedroom farmhouse farm stay.

9. 5BR Berkshire Home Mins To The Mountain

10. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

11. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

12. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

14. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

15. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

16. NEW RENO - Chalet-style farm loft near Tanglewood

17. Bear Creek Cabin

18. Real Estate: Therapy - Lake, Laundry, Love it

19. The Greylock Cabin

20. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Berkshire Mountain Lodge

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Berkshires Untold

The Red Lion Inn

Frequently asked questions

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