Discover Your Perfect Conway Vacation Homes

Conway Luxury Rentals

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Conway Pet Friendly Vacation Rentals

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9.3 (11 Reviews)
Bed & Breakfast
Cavalier Cottage B&B
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Conway Large Vacation Homes

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Why Choose Rent By Owner for your Conway Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Conway

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience and ensure you enjoy the region’s unique charm at its best, whether you're seeking outdoor adventures or a peaceful retreat in the area’s scenic surroundings.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences warm weather ideal for outdoor activities and exploring the scenic region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn brings vibrant foliage and mild temperatures, making it a perfect time to enjoy the area's natural beauty and outdoor pursuits.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

The winter season offers a tranquil atmosphere with cooler temperatures, ideal for cozy getaways and scenic winter views.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
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Spring (March to May)

Springtime sees milder weather and blooming landscapes, perfect for visiting before the busy summer season begins.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Conway

How to Book Your Conway Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Conway

More Top-Rated Vacation Rentals in Conway Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor gatherings and barbecues with a private grill in the region’s scenic settings.
  • Relax on a spacious patio or deck overlooking the natural beauty of this destination.
  • Take advantage of on-site parking to easily explore the area's outdoor attractions.
  • Make use of a fire pit for cozy evenings under the stars after daytime adventures.
  • Benefit from access to well-maintained gardens or lawn areas ideal for outdoor activities.
  • Utilize outdoor seating areas designed for enjoying the fresh air and mountain views.
  • Participate in recreational activities such as hiking, biking, or birdwatching right from your rental’s doorstep.

Top Attractions Around Conway

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic trails that showcase the natural beauty surrounding Conway, Massachusetts.

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Family Activities

  • Hiking at Mount Greylock State Reservation: Explore scenic trails with your family, offering spectacular views and a chance to enjoy the natural beauty of this region.
  • Visit the Conway Scenic Railroad: Experience a nostalgic train ride through the picturesque countryside that provides fun for all ages in this area.
  • Fishing in the local lakes and rivers: Spend a relaxing day casting lines in nearby waterways that are perfect for family fishing adventures.
  • Explore the fields and forests at Beartown State Forest: Discover outdoor activities such as picnicking and wildlife observation in this tranquil natural setting.
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Adult Activities

  • Conway Scenic Railroad: Experience a scenic train ride through the picturesque landscape of the region, offering stunning views and a relaxing way to explore the area's natural beauty.
  • Hiking at Mount Greylock State Reservation: Embark on hiking adventures in the nearby state reservation, where trails lead to panoramic vistas and serene woodland settings.
  • Exploring Berkshire Botanical Garden: Visit this beautifully maintained garden to enjoy diverse plant collections and tranquil outdoor spaces, perfect for leisurely strolls.
  • Shopping and Dining in Downtown Conway: Discover local shops and eateries that showcase regional flavors and craftsmanship, enriching your stay in the area.

Other Places to Stay in Conway, MA

South Centre/Pumpkin Hollow Cemetery
South Centre/Pumpkin Hollow Cemetery Vacation Rentals
Bardwell's Ferry Bridge
Bardwell's Ferry Bridge Vacation Rentals
Conway Town Park
Conway Town Park Vacation Rentals
Field Memorial Library
Field Memorial Library Vacation Rentals
Pine Grove Cemetery
Pine Grove Cemetery Vacation Rentals
Howland Cemetery
Howland Cemetery Vacation Rentals
More Places to Stay Near Conway

Conway Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Natural Attractions: Take advantage of the area's scenic beauty by visiting nearby parks and outdoor spaces to enjoy the region's stunning landscapes.
  • Experience Seasonal Activities: Plan your itinerary around seasonal events and outdoor activities that showcase the region’s unique climate and cultural offerings.
  • Choose a Central Location: Select a vacation rental strategically situated to give you easy access to the area's main attractions and points of interest.
  • Plan in Advance During Peak Seasons: Book your vacation rentals early to secure the best properties and avoid the rush during busy travel periods in this destination.

Transportation Options

  • Conway Area Bus Service: This local bus service offers convenient transportation within the region, making it easy to explore Conway's scenic surroundings without a car.
  • Regional Airport (Hancock Field): Situated nearby, this airport provides travelers with a quick and accessible option to fly into the area for your stay in Conway.
  • Rental Car Services: Numerous rental agencies operate here, giving you the flexibility to explore the picturesque region at your own pace during your visit.
  • Taxi and Rideshare Options: Taxis and rideshare services are readily available for effortless travel around Conway and its neighboring attractions.

Local Customs Options

  • Local Craftsmanship: You’ll notice a strong tradition of handcrafted pottery and woodworking, reflecting the region’s appreciation for artisanal skills.
  • Seasonal Festivals: Participating in seasonal festivals allows you to embrace the area's vibrant community spirit and celebrate local traditions throughout the year.
  • Farm-to-Table Dining: Enjoy the region's emphasis on fresh, locally sourced ingredients, which is a cornerstone of its culinary customs.
  • Respect for Nature: The area values environmental conservation and outdoor etiquette, encouraging visitors to preserve its scenic beauty during their stay.

Frequently Asked Questions About Conway?

1. What are the top vacation rentals in Conway?

There are a lot of options in Conway. If you plan on staying in the Conway area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Conway:

2. How many vacation rentals have private pools in Conway?

There are 2 vacation rentals with private pools near Conway. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Conway are best for families?

If you are looking for a family-friendly vacation home in Conway, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Conway:

4. How many Rentbyowner vacation rentals are available in Conway?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 155 in the Conway 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 Conway. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies by property, so you should review the specific listing details or contact the owner directly to understand the terms and any potential fees.

6. How do I inquire about available dates and booking options for my stay?

You can check the availability calendar on the property listing and reach out to the owner with your preferred dates to confirm booking options.

7. Are there any specific house rules or amenities I should be aware of before booking?

Each vacation rental has its own set of house rules and amenities listed in the property description. It's recommended to read these details carefully or ask the owner for additional information.

8. What safety measures are in place at vacation rentals here to ensure a secure stay?

Safety features vary by property, but many listings include details about security measures such as lockable doors, smoke detectors, and outdoor lighting. Contact the owner if you need further assurance.

9. Is there a minimum stay requirement at vacation rentals in this destination?

Minimum stay requirements depend on the individual property; please review the listing or contact the owner directly to confirm any restrictions.