Windsor Condominium Resort Rental from CA $94

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Recommended hotels in Windsor

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

1. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

CA $139 total

includes taxes & fees

Sep 8 - Sep 9

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

2. The Yankee Inn

Lenox

Karen

CA $163 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

3. FairBridge Inn Express

Pittsfield

ERICIA

CA $94 total

includes taxes & fees

Sep 7 - Sep 8

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

CA $182 total

includes taxes & fees

Sep 9 - Sep 10

A living room with a fireplace, two sofas, and four black side tables.

5. The Revival House

Adams

James

CA $256 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

6. Berkshire Mountain Lodge

Pittsfield

Robert

CA $154 total

includes taxes & fees

Oct 1 - Oct 2

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

7. Howard Johnson by Wyndham Lenox

Lenox

irene

CA $121 total

includes taxes & fees

Sep 7 - Sep 8

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

8. Rodeway Inn

Adams

Brandie

CA $112 total

includes taxes & fees

Oct 5 - Oct 6

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

9. Berkshire Inn

Pittsfield

Ellen

CA $129 total

includes taxes & fees

Oct 7 - Oct 8

An indoor swimming pool with clear water, tiled floors, and a blue wall.

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Steve

CA $196 total

includes taxes & fees

Sep 10 - Sep 11

A building entrance with a large planter with purple flowers and a small tree.

11. Hotel On North

Pittsfield

Drew

CA $208 total

includes taxes & fees

Sep 7 - Sep 8

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

12. The Central Downtown Inn & Suites

Pittsfield

Rena

CA $153 total

includes taxes & fees

Sep 7 - Sep 8

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

13. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

CA $267 total

includes taxes & fees

Sep 22 - Sep 23

A spacious hotel lobby with multiple seating areas, large windows, and a television.

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

CA $200 total

includes taxes & fees

Sep 30 - Oct 1

A patio area with outdoor furniture, a fire pit, and potted plants.

15. The Springs Motel

New Ashford

Elizabeth

CA $181 total

includes taxes & fees

Sep 13 - Sep 14

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

16. Harbour House Inn

Cheshire

Gregory

CA $338 total

includes taxes & fees

Sep 8 - Sep 9

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

17. Vacation Village in the Berkshires

Williamstown

Alex

CA $162 total

includes taxes & fees

Sep 15 - Sep 16

A building with a covered parking area and a grassy front yard.

18. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

CA $155 total

includes taxes & fees

Sep 7 - Sep 8

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

19. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Basil

CA $221 total

includes taxes & fees

Sep 27 - Sep 28

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

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

Dalton

Elizabeth G.

CA $452 total

includes taxes & fees

Sep 10 - Sep 11

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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"

The Whitlock

10/10 Excellent

"The Inn was quaint and conveniently situated in downtown Lenox near shops and restaurants and a short drive to Tanglewood. The virtual check-in worked seamlessly, and a friendly, helpful staff member greeted us at the front desk. Our King Room was clean, comfortable and attractive - perfect for our overnight getaway."

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. Our room was very large with a sitting area + TV. Bed room area equally as large, also with a TV. The bathroom was gorgeous with thoughtful touches. On the marble counter was a makeup mirror with a stool so one could sit. Parking lot was in rear of hotel, secure and easy access to the lobby. Staff couldn't have been more accessible and pleasant. Highly recommend this hotel"

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Find out more about Windsor

Windsor Condo Resorts information

Number of reviews	7,850
Accommodation	0 Condo Resorts
Lowest Price	CA $94
Highest Price	CA $452

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Dalton Vacation Rentals

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Windsor

1. Best Western Plus Berkshire Hills Inn & Suites

2. The Yankee Inn

3. FairBridge Inn Express

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

5. The Revival House

6. Berkshire Mountain Lodge

7. Howard Johnson by Wyndham Lenox

8. Rodeway Inn

9. Berkshire Inn

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

11. Hotel On North

12. The Central Downtown Inn & Suites

13. The Trail in Adams - Berkshires’ Art Hotel

14. Hampton Inn & Suites Berkshires-Lenox

15. The Springs Motel

16. Harbour House Inn

17. Vacation Village in the Berkshires

18. Howard Johnson by Wyndham Williamstown

19. Hotel Downstreet, an Ascend Collection Hotel

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

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Whitlock

Hotel On North

Vacation Village in the Berkshires

Willows Motel Williamstown

Quality Inn Lee - Lenox South

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

The Red Lion Inn

Find out more about Windsor

Windsor Condo Resorts information

Explore a world of travel with Expedia

Find and Compare Windsor Condo Resort Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Windsor

1. Best Western Plus Berkshire Hills Inn & Suites

2. The Yankee Inn

3. FairBridge Inn Express

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

5. The Revival House

6. Berkshire Mountain Lodge

7. Howard Johnson by Wyndham Lenox

8. Rodeway Inn

9. Berkshire Inn

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

11. Hotel On North

12. The Central Downtown Inn & Suites

13. The Trail in Adams - Berkshires’ Art Hotel

14. Hampton Inn & Suites Berkshires-Lenox

15. The Springs Motel

16. Harbour House Inn

17. Vacation Village in the Berkshires

18. Howard Johnson by Wyndham Williamstown

19. Hotel Downstreet, an Ascend Collection Hotel

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

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Windsor

Windsor Condo Resorts information

Explore a world of travel with Expedia