Glendale Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Glendale, Massachusetts, USA

Beautiful House in the Woods, Huge Yard, Hot Tub
10.0 (1 Review)
4 Bedrooms 8 Guests
Tranquil 3 BR Stockbridge House w/Private Deck!
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9.5 (2 Reviews)
3 Bedrooms 6 Guests
The Little Lion
FromUS $156 per night
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8.6 (588 Reviews)
1 Bedroom 2 Guests
Stockbridge Country Inn
FromUS $314 per night
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9.3 (18 Reviews)
8 Bedrooms 16 Guests
Deluxe cottage retreat!
FromUS $468 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
Great Barrington Lakeside Getaway w/Kayak & Grill
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9.3 (3 Reviews)
4 Bedrooms 10 Guests
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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9.0 (2 Reviews)
2 Bedrooms 4 Guests
Beachwood Cottage
FromUS $321 per night
9.8 (6 Reviews)
2 Bedrooms 6 Guests
Lakefront Berkshires Retreat w/Deck, Dock & Boat!
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7.5 (4 Reviews)
4 Bedrooms 10 Guests
Private Home Overlooking Stevens Lake
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New
6 Bedrooms 6 Guests
Cozy Cabin on Lake Mahkeenac
9.0 (12 Reviews)
2 Bedrooms 4 Guests
Classic Stockbridge Cottage
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New
4 Bedrooms 8 Guests
Pond & Hot Tub! Airy Hudson Valley Escape
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New
3 Bedrooms 12 Guests
Suite 4 - Quiet and private accommodations in a country setting.
10.0 (3 Reviews)
1 Bedroom 2 Guests
Spencertown Inn
FromUS $254 per night
10.0 (8 Reviews)
6 Bedrooms 18 Guests
The Little Lion
FromUS $115 per night
7.4 (193 Reviews)
16 Bedrooms 8 Guests
Tranquil 3 BR Stockbridge House w/Private Deck!
10.0 (97 Reviews)
3 Bedrooms 6 Guests
Classic Stockbridge Cottage
10.0 (19 Reviews)
4 Bedrooms 8 Guests
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
10.0 (11 Reviews)
3 Bedrooms 6 Guests
Beautiful House in the Woods: Huge Yard, Hot Tub
10.0 (10 Reviews)
4 Bedrooms 8 Guests
Spacious & Modern Berkshires Getaway
10.0 (9 Reviews)
3 Bedrooms 7 Guests
Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!
10.0 (6 Reviews)
3 Bedrooms 6 Guests
1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge
10.0 (4 Reviews)
4 Bedrooms 8 Guests
Lakeshore cabin with beach and dock
10.0 (4 Reviews)
3 Bedrooms 7 Guests
Sunset River Views, SIP, Spotless, Sleeps 8
10.0 (3 Reviews)
3 Bedrooms 8 Guests
Peaceful Woodland Home in the Heart of the Berkshires
9.8 (53 Reviews)
3 Bedrooms 8 Guests
Cozy Riverside Berkshires Retreat
9.6 (21 Reviews)
3 Bedrooms 8 Guests
Great Barrington Lakeside Getaway w/Kayak & Grill
9.2 (20 Reviews)
4 Bedrooms 10 Guests
Grandparent’s Cottage 250 steps to the lake
8.0 (1 Review)
4 Bedrooms 7 Guests
Fall Weekends and Ski Season is here!
New
3 Bedrooms 6 Guests
Pond & Hot Tub! Airy Hudson Valley Escape
9.6 (5 Reviews)
3 Bedrooms 12 Guests
Quiet 3BR Home, Near Tanglewood in Stockbridge
10.0 (1 Review)
3 Bedrooms 6 Guests
Stay Lakeside This Summer!
9.8 (80 Reviews)
3 Bedrooms 6 Guests
Stockbridge Bowl Lake Community
9.8 (11 Reviews)
4 Bedrooms 6 Guests
Beautiful House In The Woods, Huge Yard, Hot Tub
9.6 (21 Reviews)
4 Bedrooms 8 Guests
The Berkshires Basecamp
FromUS $605 per night
New
5 Bedrooms 10 Guests
Rustic Getaway with Extraordinary Vista
New
4 Bedrooms 10 Guests
Greek Revival Farmhouse in Stockbridge
New
3 Bedrooms 6 Guests
Canary House: ski house near Butternut!
9.0 (2 Reviews)
2 Bedrooms 4 Guests
Stockbridge Cottage minutes from downtown Lenox
5.0 (14 Reviews)
3 Bedrooms 7 Guests
ESCAPE to STOCKBRIDGE|SKI & EXPLORE|The BERKSHIRES|
4.7 (39 Reviews)
4 Bedrooms 9 Guests
Cozy Secluded Cabin in the Berkshires
4.6 (14 Reviews)
3 Bedrooms 7 Guests

About Glendale Vacation Rentals

With more than 68 Glendale vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Glendale.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Glendale, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Glendale. Places to stay near Glendale are 1037.57 ft² on average, with prices averaging US $487 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Glendale with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Glendale?

What are the top vacation rentals in Glendale?

How many Rentbyowner vacation rentals are available in Glendale?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Glendale area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Glendale.