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Jan 9 - Jan 11
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Jan 16 - Jan 18
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Jan 30 - Feb 1
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Feb 27 - Mar 1
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Recommended hotels in Monterey

Fridge, microwave, oven, stovetop
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Vacation Home in Monterey

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
$1,565 nightly
The price is $1,748
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1002)
"Very friendly and good Breakfast."
United States
Jesse
$76 nightly
The price is $85
Jan 3 - Jan 4, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
$135 nightly
The price is $151
Jan 7 - Jan 8, 2026
Total with taxes and fees
Element Lenox Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
$88 nightly
The price is $99
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Motel in Great Barrington

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (565)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Jan 1 - Jan 2, 2026
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
8.4 out of 10, Very Good, (1002)
"Safe, clean rooms, decent breakfast "
United States
Neil
$84 nightly
The price is $94
Jan 18 - Jan 19, 2026
Total with taxes and fees
Quality Inn Lee - Lenox South
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
$98 nightly
The price is $109
Jan 25 - Jan 26, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Garden
Shaker Mill Inn

Bed & Breakfast in West Stockbridge

Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (439)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
$105 nightly
The price is $116
Jan 6 - Jan 7, 2026
Total with taxes and fees
Shaker Mill Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$101 nightly
The price is $113
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$104 nightly
The price is $116
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
$128 nightly
The price is $143
Jan 3 - Jan 4, 2026
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Motel in Great Barrington

Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (811)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Jan 1 - Jan 2, 2026
Total with taxes and fees
Monument Mountain Motel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Motel in Pittsfield

Berkshire Inn
2.0 star property
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$79 nightly
The price is $89
Jan 5 - Jan 6, 2026
Total with taxes and fees
Berkshire Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Very comfortable beds! "
United States
Gerald
$109 nightly
The price is $122
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Exterior
Howard Johnson by Wyndham Lenox

Motel in Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Jan 1 - Jan 2, 2026
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
8.4 out of 10, Very Good, (1000)
"My go to place for my ski weekends"
United States
Ryan
$76 nightly
The price is $85
Jan 14 - Jan 15, 2026
Total with taxes and fees
Quality Inn Great Barrington
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.2 out of 10, Wonderful, (71)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
$123 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Terrace/patio
Locust Tree Bed and Breakfast LLC

Bed & Breakfast in East Canaan

Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Jan 1 - Jan 2, 2026
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
$135 nightly
The price is $151
Jan 19 - Jan 20, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect Berkshires
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 Monterey Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!"
Michie 3-night trip
Posted 18 hours ago
Prospect Berkshires

Find out more about Monterey

Monterey Condo Rentals information

Number of reviews
13,078
Accommodation
10 Condo Rentals
Lowest Price
$74
Highest Price
$1,748

Frequently asked questions

Why book your condo in Monterey with Expedia?
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How can I find cheap condos in Monterey?
A great way to score cheap condos in Monterey is with Expedia's nifty filter tool. Narrow your search by budget, star rating and amenities to take advantage of awesome bargains in a few clicks.
What is there to do in Monterey near my condo?
If you're eager to discover the sights of Monterey, make your way to Bidwell House Museum. It's a hit among tourists and locals alike.

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