Hotels in Stockbridge, MA: Compare 10+ Sites & Save

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52 Best Hotels in Stockbridge (Starting from $79)

The Red Lion Inn
The Red Lion Inn
Hotel
Stockbridge, MA, USA
0.9k from Stockbridge center

Accommodations, Pools, Parking, Romantic, Boutique, Pet-friendly, 4-star, Lodgings, Hot tubs

8.2

Very Good

296 reviews

$308
Average price / night
Check Availability
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires
Hotel
South Lee, MA, USA
4.0k from Stockbridge center

Accommodations, Pools, Parking, Holiday inn , 3-star, Lodgings, Hot tubs, Places to stay, Family

8.8

Fabulous

639 reviews

$183
Average price / night
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Great Place - 2 BD - Kitchen - Pool 
Great Place - 2 BD - Kitchen - Pool 
Hotel
Lee, MA, 01238, United States
3.9k from Stockbridge center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

9.6

Exceptional

5 reviews

$260
Average price / night
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Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
Hotel
Stockbridge, Massachusetts, USA
5.5k from Stockbridge center

Accommodations, Motels, Parking, Lodgings, Places to stay

5.4

Review score

116 reviews

$79
Average price / night
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hotel
190 Meadow Street, South Lee, MA, 01260, United States
4.0k from Stockbridge center

AC, Arcade, Balcony, Bar, Barbecue, Business Services, Crib, Heater, Internet

9.0

Fabulous

861 reviews

$153
Average price / night
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The Little Lion
The Little Lion
Hotel
Stockbridge, Massachusetts, USA
5.5k from Stockbridge center

Cheap, Accommodations, Motels, Parking, Romantic, Pet-friendly, Lodgings, Places to stay, Family

7.2

Good

218 reviews

$175
Average price / night
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Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks
Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

8.8

Fabulous

13 reviews

$196
Average price / night
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The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel
Lee, MA, USA
6.0k from Stockbridge center

Cheap, Accommodations, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay, Accessible hotels

8.6

Fabulous

532 reviews

$178
Average price / night
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Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone
Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

10.0

Exceptional

4 reviews

$394
Average price / night
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Seven Hills Inn
Seven Hills Inn
Hotel
Lenox, MA, USA
6.1k from Stockbridge center

Air Conditioner, Pool, Parking, Smoking, Internet, Pet Friendly, Wheelchair Accessible

7.9

Good

345 reviews

$171
Average price / night
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Scenic Escape: Full Kitchen, Pools, Game Room & Outdoor Fun
Scenic Escape: Full Kitchen, Pools, Game Room & Outdoor Fun
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$196
Average price / night
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Lakehouse Inn
Lakehouse Inn
Hotel
Stockbridge, Massachusetts, USA
6.2k from Stockbridge center

B&bs, Cheap, Accommodations, Parking, Inns, Lodgings, Places to stay, Accessible hotels, Ski resorts

9.3

Superb

147 reviews

$175
Average price / night
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Two Spacious Villas | Indoor Pools, Game Nights & Nature Trails – All-in Escape
Two Spacious Villas | Indoor Pools, Game Nights & Nature Trails – All-in Escape
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$394
Average price / night
Check Availability
Pilgrim Inn
Pilgrim Inn
Hotel
Lee, MA, USA
6.3k from Stockbridge center

B&bs, Accommodations, Parking, Inns, Pet-friendly, Lodgings, Places to stay, Family

5.3

Review score

539 reviews

$99
Average price / night
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Three Villas, Endless Play | Indoor Pools, Trails, Games &  BBQ Decks
Three Villas, Endless Play | Indoor Pools, Trails, Games & BBQ Decks
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$590
Average price / night
Check Availability
Quality Inn
Quality Inn
Hotel
Lee, MA, USA
6.3k from Stockbridge center

Hot Tub, Air Conditioner, Smoking, Parking, Eco Friendly, Security/Safety, Accessibility

8.2

Very Good

478 reviews

$110
Average price / night
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Big Chill + Big Thrill | Three 2BR Villas w/ Pools, Sauna & Arcade Fun
Big Chill + Big Thrill | Three 2BR Villas w/ Pools, Sauna & Arcade Fun
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$590
Average price / night
Check Availability
Sunset Inn
Sunset Inn
Hotel
Lee, MA, USA
6.3k from Stockbridge center

Accommodations, Pools, Motels, Parking, 3-star, Lodgings, Places to stay, Accessible hotels

7.6

Good

102 reviews

$90
Average price / night
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All Season Escape | Four 2BR Rooms, Pools, Movie Nights & Game Room Galore
All Season Escape | Four 2BR Rooms, Pools, Movie Nights & Game Room Galore
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$788
Average price / night
Check Availability
Apple Tree Inn
Apple Tree Inn
Hotel
Lenox, MA, USA
7.2k from Stockbridge center

B&bs, Accommodations, Pools, Parking, Inns, Lodgings, Places to stay, Family

8.5

Very Good

249 reviews

$191
Average price / night
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Play, Soak, Repeat | 4 Spacious Villas w/ Pools, Game Room, Trails & BBQ Decks
Play, Soak, Repeat | 4 Spacious Villas w/ Pools, Game Room, Trails & BBQ Decks
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

New to Booking
$788
Average price / night
Check Availability
Thornewood Inn
Thornewood Inn
Hotel
Stockbridge, Massachusetts, USA
7.5k from Stockbridge center

Pet Friendly, Wheelchair Accessible, Balcony/Terrace, Air Conditioner, Pool, Internet, Breakfast

7.9

Good

18 reviews

$179
Average price / night
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Relaxing Getaway: Pools, Games & Movie Nights
Relaxing Getaway: Pools, Games & Movie Nights
Hotel
Lee, MA, 01260, United States
4.1k from Stockbridge center

AC, Arcade, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

9.0

Fabulous

8 reviews

$196
Average price / night
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Hampton Terrace Inn
Hampton Terrace Inn
Hotel
MA, USA
8.0k from Stockbridge center

Accommodations, Pools, Parking, Spa, 4-star, Lodgings, Jacuzzis, Places to stay, Family

9.5

Superb

20 reviews

$219
Average price / night
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The Constance by The Lenox Collection
The Constance by The Lenox Collection
Hotel
Stockbridge, Massachusetts, USA
8.0k from Stockbridge center

B&bs, Accommodations, Parking, Inns, Pet-friendly, 4-star, Lodgings, Vacation rentals, Places to stay

8.2

Very Good

492 reviews

$165
Average price / night
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Doctor Sax House
Doctor Sax House
Hotel
Lenox, MA, USA
8.1k from Stockbridge center

Luxury, Cheap, Accommodations, Parking, Pet-friendly, 4-star, Lodgings, Places to stay, Family

8.9

Fabulous

10 reviews

$505
Average price / night
Check Availability
33 Main
33 Main
Hotel
Lenox, MA, USA
8.2k from Stockbridge center

B&bs, Accommodations, Parking, Inns, Lodgings, Places to stay

8.6

Fabulous

23 reviews

$489
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Hotels in Stockbridge.

Stay Near Stockbridge's Top Attractions

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Stockbridge Hotels on the Map

Frequently Asked Questions

You can explore 52 verified hotels in Stockbridge. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Stockbridge vary depending on the season, location, and property type. Rates typically start from around $79 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Stockbridge include amenities such as Sports/Activities, Entertainment, and Pool. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Stockbridge by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Stockbridge welcome pets. Currently, 9 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Stockbridge offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.