Vacation rentals in Massey

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Top-rated vacation rentals in Massey

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Guest favorite

Farm stay in Chestertown

4.95 out of 5 average rating, 148 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Top guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 235 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Guest favorite

Cottage in Charlestown

4.95 out of 5 average rating, 206 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Guest favorite

Home in Galena

4.94 out of 5 average rating, 49 reviews

Connection Pointe•River views•Quiet•Peaceful

Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.

Guest favorite

Apartment in Clayton

4.93 out of 5 average rating, 58 reviews

Quaint 1st floor 1 BR apt in Historic Firehouse

1 bedroom apt. in historic building in town (1800's Firehouse). Newly remodeled for those looking for quaint getaway. Within sight of small park with gazebo, coffee shop (old Town hall), 1 block to local pizza shop. Just a short drive to Smyrna where you will find anything else you are needing. Central to the beach, the bay, Baltimore, Philadelphia, Lancaster, and so many small towns along the way. Anything you dont find in Smyrna we have Dover to the south or Middletown to the north.

Top guest favorite

Home in Millington

5 out of 5 average rating, 35 reviews

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Guest favorite

Home in Warwick

4.95 out of 5 average rating, 19 reviews

Saybrook Hall | Pickleball + Pool + Hot Tub

BNB Breeze Presents: Saybrook Hall! Discover the perfect getaway in this spacious rental home in Maryland, and stay in a real life colonial home! The original house sat in Connecticut and was disassembled to be built into a newer modern version here in Warwick, MD. Featuring a charming rustic design with wooden beams and cozy accents, this home seamlessly blends traditional warmth with modern amenities. - Pickleball/basketball Court - Pool - Hot Tub - Chipping Green - Pizza Oven

Guest favorite

Camper/RV in Hartly

4.85 out of 5 average rating, 34 reviews

Cozy Camper Escape Near Dover

Escape to a cozy camper in Hartly, DE! This stylish retreat sleeps 3 with a queen sized bed with memory foam mattress, and pull-out sofa. Enjoy amenities like AC, a fridge, freezer, 3-burner gas stove, oven, and instant hot water. A space heater is provided for chilly nights. Just 20 minutes from Dover attractions like Dover Motor Speedway and Delaware State University, it’s perfect for a peaceful getaway or event-filled stay. Book today for comfort and convenience!

Guest favorite

Guesthouse in Dover

4.87 out of 5 average rating, 143 reviews

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Guest favorite

Home in Millington

4.95 out of 5 average rating, 38 reviews

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

Guest favorite

Apartment in Dover

4.89 out of 5 average rating, 155 reviews

Cozy apartment in a quiet Amish country setting

Relax in our fully furnished 1 bedroom (and a spare room with a futon for extra bedding ) 1 bath, living room, and kitchenette apartment, with a private ground level entrance, in a peaceful Amish country setting. The unit is 5 miles away from the Dover city limits. While here, be sure to enjoy shopping at Byler’s Store, a local destination stop featuring a deli, bakery, grocery and gift shop.

Guest favorite

Home in Millington

4.88 out of 5 average rating, 73 reviews

The Peaceful Getaway (with private pool & hot tub)

Kick back and relax at this charming peaceful getaway, the perfect place to enjoy with friends and family! This beautiful 2 story spacious house is back off a dead end road, but still only minutes from the main highway. It’s very private with a beautiful in ground pool and hot tub behind the house! And also lots of space for outdoor cooking. Please no pets