Old Mansions - Vacation Rentals in Montgomery

Historic Farmhouse Near Mountains and Colleges! From US $421
         

Easthampton Vacation Rental - Walk to Breweries! From US $256
         

Big farmhouse in the foothills of the Berkshires From US $367
         

10.0 (143 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating From US $174
         

The Creation Station is a cozy place so make yourself at home. From US $216
         

Luxury Places to Stay in Montgomery

Over 192+ Luxury Places to Stay in or Near Montgomery
Hill Ross Farmhouse Historic Homestead From US $958
         

10.0 (3 Reviews)
Other
  • Air Conditioner
  • Parking
  • TV
Button's Modern Luxury Walkup Downtown Northampton From US $608
         

Lakefront Bungalow From US $599
         

9.8 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Montgomery

Over 28+ Top-Rated Vacation Rentals with a Pool in or Near Montgomery
D. Hotel Suites & Spa From US $116
         

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9.2 (2237 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Fairfield Inn & Suites Springfield Northampton/Amherst From US $141
         

Hotel Northampton From US $184
         

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9.2 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites Springfield Holyoke From US $132
         

9.2 (592 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott West Springfield From US $135
         

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9.2 (580 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Holyoke-Springfield/North From US $133
         

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9.0 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Montgomery

Over 59+ Pet-Friendly Vacation Rentals in or Near Montgomery
My Lake House w/dock and kayaks From US $313
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bring Your Pet and Visit Springfield Westfield Home From US $178
         

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9.5 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Red Roof Inn PLUS+ West Springfield From US $95
         

6.8 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Serene 3-BR Berkshires Log Cabin From US $443
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Berkshires Vacation Rental Near Hiking! From US $177
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cheerful 1 bedroom From US $227
         

9.8 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pristine Home In Becket Woods From US $289
         

9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Montgomery

Over 13+ Large Vacation Homes & Villas in or Near Montgomery
Thrill & Chill Ski & Sauna In Winter Wonderland From US $533
         

9.3 (3 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Security/Safety
Pet-Friendly Westfield Home w/Fenced Yard! From US $269
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Montgomery

Over 20+ Wheelchair Accessible Vacation Homes in or Near Montgomery
New In-Law Apartment/Private Entry From US $122
         

4.5 (29 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Blue - A Modern Hotel, an Ascend Collection Hotel From US $141
         

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9.1 (35 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Homewood Suites by Hilton Holyoke-Springfield/North From US $190
         

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8.6 (197 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn by Marriott West Springfield From US $135
         

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8.6 (517 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott West Springfield From US $152
         

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8.6 (138 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hampton Inn Westfield From US $115
         

8.4 (815 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Candlewood Suites-West Springfield by IHG From US $162
         

8.3 (221 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Montgomery Varoom and Airbnb Places to Stay Under $200

Over 76+ Montgomery Varoom and Airbnb Places to Stay Under $200
Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College From US $147
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Cozy First Floor Apartment From US $188
         

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8.9 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ellery From US $133
         

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9.2 (908 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Welcoming studio near Holyoke Medical Center + free wifi From US $153
         

Cozy apartment near I91 & Holyoke Medical Center + wifi From US $185
         

Elm Suite with a Private Bathroom in front of Smith College Quadrangle From US $143
         

Easthampton Vacation Rental - Walk to Breweries! From US $159
         

9.4 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy First Floor Apartment. Located in a quiet neighborhood. From US $198
         

9.2 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Montgomery

Over 51+ Instantly Bookable Vacation Homes in or Near Montgomery
Historic Farmhouse Near Mountains & Colleges! From US $290
         

Hill Ross Guest Suite on Historic Homestead From US $503
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Townhouse with Pool Table - Renovated w/King Bednn From US $385
         

Home in the Woods From US $323
         

10.0 (3 Reviews)
House
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
Cabin Style Rustic Getaway, with mini-splits From US $236
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Montgomery Vacation Rentals

With more than 201 Montgomery vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Old Mansions 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 a rental property in Montgomery.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Old Mansions Montgomery, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner 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, and other popular Airbnb-style properties in Montgomery. Places to stay near Montgomery are 931.84 ft² on average, with prices averaging $356 a night.

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

Top Rental Accommodation Types in Montgomery

Type Count
Vacation Homes 75
Holiday Apartments 55
Hotels with Suites 46
Cottages 9
Cabin Rentals 7
Others 5
Ski Chalet Rentals 2

Use these Quick Filters to Find a Vacation Rental in Montgomery

Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Montgomery.

Weather in Montgomery

View the weather forecast for Montgomery before booking your Montgomery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F