Montgomery Holiday Rentals
- Massachusetts
- ·
- Otis
- 3.70 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Parking
- Internet
- Child Friendly
- Security/Safety
- Springfield
- ·
- Holyoke
- 1.14 mi to center
- Kitchen
- Parking
- Air Conditioner
- Internet
- Springfield
- ·
- Chicopee
- 2.18 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
- Springfield
- ·
- Chicopee
- 1.32 mi to center
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Kitchen
- Parking
- Air Conditioner
- Internet
- Springfield
- ·
- Chester
- 1.25 mi to center
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
- Security/Safety
- Massachusetts
- ·
- Otis
- 2.18 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Otis
- 4.27 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Luxury Holiday Rentals in Montgomery
- Springfield
- ·
- Florence
- 0.62 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Kitchen
- Parking
- Air Conditioner
- Internet
- Springfield
- ·
- Florence
- 0.79 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Springfield
- ·
- Blandford
- 4.66 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Otis
- 2.55 mi to center
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Massachusetts
- ·
- Westhampton
- 2.17 mi to center
- Pet Friendly
- Parking
- Internet
- Child Friendly
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Parking
- Internet
- Child Friendly
- Security/Safety
- Massachusetts
- ·
- Westhampton
- 2.17 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Massachusetts
- ·
- Otis
- 3.70 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
Top-Rated Holiday Rentals with a Pool in Montgomery
- Springfield
- ·
- Easthampton
- 1.70 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Springfield
- ·
- Blandford
- 3.20 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Springfield
- ·
- Holyoke
- 4.65 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Springfield
- ·
- Northampton
- 0.37 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
- Springfield
- ·
- Northampton
- 0.51 mi to center
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
- Springfield
- ·
- Holyoke
- 2.54 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Springfield
- ·
- West Springfield
- 1.56 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Springfield
- ·
- Holyoke
- 3.14 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
- Springfield
- ·
- Holyoke
- 4.57 mi to center
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
Pet-Friendly Holiday Rentals in Montgomery
- Becket
- ·
- Sherwood Forest
- 0.53 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Springfield
- ·
- Westfield
- 2.14 mi to center
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
- Springfield
- ·
- West Springfield
- 2.30 mi to center
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
- Massachusetts
- ·
- Otis
- 2.33 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Springfield
- ·
- Westfield
- 2.35 mi to center
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
- Springfield
- ·
- Chicopee
- 1.20 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Massachusetts
- ·
- Otis
- 3.61 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Otis
- 4.47 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
- Springfield
- ·
- Montgomery
- 1.41 mi to center
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
Large Holiday Rentals and Private Villas in Montgomery
- Massachusetts
- ·
- Otis
- 3.93 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Otis
- 2.57 mi to center
- Fireplace/Heating
- Air Conditioner
- Child Friendly
- Barbecue/Outdoor Cooking
- Becket
- ·
- Sherwood Forest
- 1.04 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Becket
- ·
- Sherwood Forest
- 1.04 mi to center
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
- Massachusetts
- ·
- Otis
- 3.36 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Springfield
- ·
- Huntington
- 5.76 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Springfield
- ·
- Blandford
- 5.54 mi to center
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Wheelchair Accessible Holiday Homes in Montgomery
- Springfield
- ·
- Westfield
- 3.98 mi to center
- Private Pool
- Pool
- Kitchen
- Air Conditioner
- Springfield
- ·
- West Springfield
- 1.95 mi to center
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
- Springfield
- ·
- West Springfield
- 1.99 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Springfield
- ·
- Holyoke
- 3.11 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Springfield
- ·
- West Springfield
- 2.34 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Springfield
- ·
- West Springfield
- 2.34 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Springfield
- ·
- West Springfield
- 1.18 mi to center
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
- Springfield
- ·
- Holyoke
- 2.45 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Springfield
- ·
- Westfield
- 2.39 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Parking
Montgomery Private Villas and Holiday Homes Under $200
- Springfield
- ·
- Florence
- 2.70 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Massachusetts
- ·
- Otis
- 4.27 mi to center
- Parking
- Internet
- Child Friendly
- Sports/Activities
- Springfield
- ·
- Northampton
- 0.77 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
- Springfield
- ·
- Florence
- 1.12 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
- Massachusetts
- ·
- Otis
- 4.47 mi to center
- Pet Friendly
- Parking
- Child Friendly
- Sports/Activities
- Springfield
- ·
- Northampton
- 0.42 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Springfield
- ·
- Northampton
- 0.30 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Springfield
- ·
- Northampton
- 0.68 mi to center
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
- Massachusetts
- ·
- Westhampton
- 0.80 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
Instantly Bookable Holiday Homes in Montgomery
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Springfield
- ·
- Russell
- 0.93 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Massachusetts
- ·
- Otis
- 2.28 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Springfield
- ·
- Westfield
- 2.12 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Springfield
- ·
- Chicopee
- 1.86 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Springfield
- ·
- Holyoke
- 0.86 mi to center
- Kitchen
- Parking
- Air Conditioner
- Internet
- Massachusetts
- ·
- Becket
- 3.35 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Springfield
- ·
- Holyoke
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Book a Last Minute Place to Stay in Montgomery
About Casai's Private Villas and Holiday Rentals in Montgomery
Discover more than 210 vacation rentals available in Montgomery. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Montgomery.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Montgomery, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Montgomery. On average, places to stay near Montgomery offer 955.88 ft², with nightly prices averaging CA $523.
With Casai, finding and comparing holiday rentals in Montgomery is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Montgomery
| Type | Count |
|---|---|
| Vacation Homes | 81 |
| Holiday Apartments | 56 |
| Cottages | 11 |
Use these Quick Filters to Find a Holiday Rental in Montgomery
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Montgomery.
Weather in Montgomery, MA
View the weather forecast for Montgomery before booking your Montgomery Vacation Rentals to confirm your best time to go.
Top Attractions Around Montgomery, MA
Casai offers a large selection of top attractions around Montgomery . Research things to do on your vacation before you visit Montgomery.
Frequently Asked Questions About Montgomery?
What are the top holiday rentals in Montgomery?
With numerous options available in Montgomery, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Montgomery:
- 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
- Big farmhouse in the foothills of the Berkshires
- Waterfront Home on Pine Island Lake
- Elegant Wilderness Cabin 12 Miles From Northampton
- Bamboo: Spacious with Cedar Wet-room, Private Patio
- Mountain View: Comfort and Calm. Wood-burning Fireplace.
- The Creation Station is a cozy place so make yourself at home.
- Gorgeous newly renovated furnished apartment
- Spacious waterfront Berkshire home family private get-away
- Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge
How many holiday rentals have private pools in Montgomery?
Discover a selection of holiday rentals with private pools near Montgomery with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Private, quiet room in a home in the suburbs. Easy access to main interstates.
- Candlewood Suites-West Springfield by IHG
- Private, Quiet Room In A Home In The Suburbs. Easy Access To Main Interstates
- Comfort Inn & Suites West Springfield
Which holiday homes in Montgomery are best for families?
If you're searching for a family-friendly holiday home in Montgomery, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Montgomery:
How many Casai.ca holiday rentals are available in Montgomery?
As of 2026, Casai boasts over 210 properties listed in the Montgomery area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Montgomery.








































































