Pigeon Bay Cottages - Vacation Rentals in Longwood

Homey Retreat in Historic Kennett Square! From US $265
         

10.0 (85 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
The Walton House - historic 3bd 2 5ba with parking From US $176
         

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10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Inn at Whitewing Farm From US $255
         

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10.0 (52 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Historic Walton House by RPG From US $719
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Carriage House in the Heart of Kennett From US $441
         

10.0 (37 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Quaint brick townhome in historic Kennett Square From US $236
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious 5-Bed Retreat in Charming Kennett Square From US $438
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Longwood

Over 31+ Luxury Places to Stay in or Near Longwood
Spacious 5-Bed Retreat in Charming Kennett Square From US $404
         

Underground Railroad 4 Bedroom Farmhouse From US $380
         

9.8 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Francis Inn & Suites From US $374
         

New
Hotel
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Luxury Loft in Historic Carriage House From US $303
         

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8.8 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Fairville Inn From US $286
         

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8.2 (479 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Historic Kennett Square From US $256
         

9.2 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Longwood

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Longwood
The Inn at Whitewing Farm From US $241
         

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8.6 (25 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Kennett Square From US $127
         

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8.4 (939 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites Kennett Square From US $170
         

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8.3 (373 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Kennett Square From US $129
         

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8.2 (151 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Longwood

Over 3+ Pet-Friendly Vacation Rentals in or Near Longwood
Underground Railroad Barn From US $195
         

9.8 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Underground Railroad Barn From US $185
         

8.5 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • View
Charming Carriage House plus 2 Longwood Tickets From US $269
         

5.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
See More Pet-Friendly Vacation Rentals in Longwood on PetFriendly.io

Large Vacation Homes & Villas in Longwood

Over 2+ Large Vacation Homes & Villas in or Near Longwood
Fairville Inn From US $240
         

9.0 (47 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in Longwood

Over 2+ Wheelchair Accessible Vacation Homes in or Near Longwood
Inn at Mendehall From US $125
         

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8.5 (413 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Inn at Mendenhall From US $138
         

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9.0 (1013 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Longwood Varoom and Airbnb Places to Stay Under $200

Over 7+ Longwood Varoom and Airbnb Places to Stay Under $200
Luxury Apartment in Kennett Square From US $190
         

9.8 (45 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Underground Railroad 3 Bedroom Farmhouse From US $170
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Artelo From US $155
         

9.8 (81 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Accessibility
The Suite in a carriage house in Kennett Square From US $198
         

9.8 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxury Loft in in Kennett Square From US $181
         

9.6 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Newly built Tiny House in Historic Kennett Square From US $173
         

Comfortable 1930s cape in Marlborough Village From US $200
         

4.9 (36 Reviews)
House
  • TV
  • Bedding/Linens
  • Child Friendly

Instantly Bookable Vacation Homes in Longwood

Over 1+ Instantly Bookable Vacation Homes in or Near Longwood
Charming Kennett Square Retreat Historic Downtown From US $224
         

9.8 (8 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Longwood Vacation Rentals

With more than 40 Longwood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Pigeonbaycottages 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 Longwood.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Pigeonbaycottages Longwood, 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 Longwood. Places to stay near Longwood are 869.86 ft² on average, with prices averaging $291 a night.

Pigeonbaycottages makes it easy and safe to find and compare vacation rentals in Longwood 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 Longwood

Type Count
Vacation Homes 19
Hotels with Suites 9
Holiday Apartments 6
B&B 5
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Longwood

Pro Tip: Pigeonbaycottages makes it easy to compare the best listings on Pigeonbaycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Pigeonbaycottages 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 Longwood.

Weather in Longwood

View the weather forecast for Longwood before booking your Longwood 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