Florida, MA Cottage Rentals

Florida Cottage Rentals

Brookside cottage near the mountains and outdoor recreation

Price Dropped

Cottage

Brookside cottage near the mountains and outdoor recreation

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests

US $202/Night 7 Nights - US $1,414

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Ski Chalet

The Mountain Cottage

2 Bedrooms 1 Bath 5 Guests 904.17 ft²

US $284/Night 7 Nights - US $1,988

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Endearing cottage in the Berkshires, walking distance to downtown and Mass MoCA.

Frequently Viewed

Cottage

Endearing cottage in the Berkshires, walking distance to downtown and Mass MoCA.

10.0

Exceptional

(17 Reviews)

2 Bedrooms 1 Bath 5 Guests

US $267/Night 7 Nights - US $1,871

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Cottage

Black Bear Mountain Cottage

2 Bedrooms 1 Bath 4 Guests

US $134/Night 7 Nights - US $937

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Cottage

Beautiful 2 bedrooms and Full Cottage Home Comfort.

2 Bedrooms 2 Baths 5 Guests 2000 ft²

US $350/Night 7 Nights - US $2,450

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House

The Greylock Cabin

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 4 Guests 880 ft²

US $374/Night 7 Nights - US $2,615

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Ski Chalet

Florida Mountain Log Cabin

10.0

Exceptional

(4 Reviews)

3 Bedrooms 1 Bath 6 Guests 904.17 ft²

US $284/Night 7 Nights - US $1,988

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Price Dropped

Bed & Breakfast

UU Rowe Camp and Conference Center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath

US $207/Night 7 Nights - US $1,448

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Cabin

Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 4 Guests

US $229/Night 7 Nights - US $1,603

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Apartment

North Adams Apartment with Renovated Kitchen

9.0

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 4 Guests 796.53 ft²

US $422/Night 7 Nights - US $2,954

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Highly Rated

House

Retreat In The Woods

9.8

Exceptional

(66 Reviews)

2 Bedrooms 1 Bath 4 Guests

US $210/Night 7 Nights - US $1,471

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Apartment

The Allen House

8.5

Fabulous

(2 Reviews)

3 Bedrooms 1 Bath 5 Guests 129.17 ft²

US $368/Night 7 Nights - US $2,578

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More Top-Rated Cottage Rentals in Florida Area

Why Choose Rent By Owner for your Florida Cottage Rentals?

What makes our Cottage Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Florida

When should you plan your Cottage Rentals stay?

To make the most of your getaway here, consider visiting during the shoulder seasons when the weather is mild and popular attractions are less crowded, allowing you to enjoy the region's natural beauty and peaceful surroundings at their best.

Peak Season Highlights

Winter (December to February)

During the winter months, you can experience milder weather and an influx of visitors seeking escape from colder climates, making this a lively period for your stay in the area.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Spring (March to May)

Spring is an ideal time to enjoy pleasant temperatures and blooming scenery, attracting travelers looking for outdoor activities and scenic retreats in this region.

Average Temperature Daytime: 75°F - Nighttime: 50°F

Off-Season Highlights

Summer (June to August)

Summertime brings warmer weather, though it’s also the quieter season for those seeking more peaceful escapes and less crowded accommodations.

Average Temperature Daytime: 85°F - Nighttime: 70°F

Fall (September to November)

Fall offers cooler temperatures and vibrant foliage, making it a perfect time for cozy stays and exploring without the peak season crowds.

Average Temperature Daytime: 70°F - Nighttime: 55°F

Weekly Weather Forecast for Florida

How to Book Your Florida Cottage Rentals

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

Book Online

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

Explore and book the perfect rental in Florida

More Top-Rated Cottage Rentals in Florida Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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 dining areas perfect for al fresco meals in this scenic region.
Take advantage of private patios or decks to relax while soaking up the sunshine.
Benefit from access to landscaped gardens that enhance your outdoor experience.
Make use of community or private swimming pools available at many properties.
Relax by outdoor fire pits, ideal for gathering with family and friends after a day of exploring.
Utilize well-maintained grilling stations for cookouts and barbecues during your stay.
Explore nearby walking trails or outdoor recreation spaces directly accessible from your cottage.

Top Attractions Around Florida

What attractions are nearby?

Within this area, you'll find an array of outdoor activities and cultural attractions that allow you to fully enjoy the vibrant surroundings, making it an ideal choice for those looking to explore nearby Florida or discover the charming towns and scenic landscapes close to Massachusetts.

Family Activities

Visit Universal Studios Florida: Enjoy a day filled with thrilling rides, live shows, and family-friendly attractions that cater to all ages in this world-famous entertainment complex.
Explore SeaWorld Orlando: Discover marine life exhibits, engaging shows, and interactive experiences perfect for a memorable family outing in the area.
Discover LEGOLAND Florida Resort: Experience imaginative play and themed rides designed specifically for children, making it ideal for families staying nearby.
Relax at the Kennedy Space Center Visitor Complex: Learn about space exploration through interactive exhibits and meet real astronauts in this inspiring destination for all ages.

Adult Activities

Florida Explore world-renowned beaches where you can enjoy sunbathing, swimming, and water sports against the backdrop of stunning coastal scenery.
Florida Visit vibrant art districts that showcase contemporary galleries, street art, and cultural events perfect for an engaging day out.
Florida Discover thrilling theme parks filled with rides, entertainment, and attractions that make for memorable adult adventures.
Florida Experience a variety of outdoor activities such as golfing on championship courses or exploring scenic nature trails in the region’s many parks.

Massachusetts Delve into the area's rich history by visiting renowned historic sites and museums that provide insights into early American culture.
Massachusetts Enjoy the lively atmosphere of local seafood restaurants and breweries that highlight the region’s culinary traditions.
Massachusetts Take part in outdoor recreational activities like sailing, kayaking, or relaxing along scenic coastal areas.
Massachusetts Explore charming cities and towns that offer boutique shopping, live entertainment, and cultural events.

Other Places to Stay in Florida, MA

Drury

Explore 61 Properties

More Places to Stay Near Florida

Florida Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead: Book your cottages well in advance to secure the best options and rates during peak seasons at popular Florida destinations and charming Massachusetts towns.
Explore Local Attractions: Take advantage of the region's unique natural and cultural sites to enrich your stay, making sure to choose a cottage location that offers easy access to these experiences.
Embrace the Outdoors: With abundant outdoor activities available, consider outdoor excursions and recreational pursuits to fully enjoy your time here by staying close to nature.
Customize Your Stay: Select a cottage that suits your needs, whether you prefer beachfront serenity or scenic woodland retreats, to create personalized memories in this destination.

Transportation Options

Rental Cars: Many visitors opt for rental cars to explore the area at their own pace and access remote cottages with ease.
Public Transit: Local bus and rail services provide affordable transportation options, making it convenient to reach various cottages across the region.
Shuttle Services: Shuttle services frequently operate between major airports and popular destinations, simplifying your journey to cottages here.
Taxis & Rideshares: Taxis and rideshare apps offer flexible and quick transportation, ideal for short trips or last-minute plans around the area.

Local Customs Options

Southern Hospitality: Expect warm welcomes and friendly interactions that reflect the region's welcoming attitude when engaging with locals here.
Respect for Nature: It’s customary to conserve resources and respect outdoor spaces, especially in areas known for their natural beauty.
Casual Dress Code: Casual and comfortable attire is typical, so dress relaxed whether you're exploring or enjoying leisure activities.
Food Traditions: Sample the local cuisine through shared meals and traditional dishes, which are integral to the area's cultural identity.

Historical Respect: When visiting historic sites or participating in local festivities, showing reverence for the region's history enhances your experience.
Community Events: Participating in community gatherings and celebrations is common and appreciated by residents seeking to preserve local customs.
Informal Greetings: Addressing neighbors and acquaintances with casual greetings is typical, fostering a friendly atmosphere throughout this destination.
Protecting Local Heritage: Supporting and respecting local traditions and practices helps maintain the area's unique cultural identity.

Florida Cottage Rentals Frequently Asked Questions

1. What are the top Cottages in Florida?

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

2. How many Cottages are available in Florida?

Currently, the total number of properties listed by RBO in 2026 is over 5 in the Florida area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Florida. 

3. What is the cancellation policy for cottages in this region?

Cancellation policies vary depending on the property owner and listing. You should review the specific terms outlined on the cottage's listing page or contact the owner directly for detailed information.

4. Are pets allowed in cottages here?

Pet policies differ among properties. To ensure your furry friend is welcome, check the pet policy listed in the cottage details or reach out to the property owner before booking.

5. How do I find cottages with flexible booking dates in this area?

Look for listings that specify flexible or adjustable booking options. You can filter search results based on your preferred stay dates or contact owners directly to inquire about flexibility.

6. What amenities are typically available in these cottages in this destination?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, heating or air conditioning, and outdoor spaces. Review each cottage’s description carefully or contact the owner to confirm what’s included.

7. Is there a minimum stay requirement for cottages in this area?

Minimum stay requirements depend on the individual listing. Check the specific booking details for each cottage or contact the owner to clarify any mandatory night stays.