Title: Greenwood Vacation Home Rentals from CA $266: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Greenwood](https://expedia.ca/Greenwood-Hotels.d110848.Travel-Guide-Hotels)[Vacation Rentals in Greenwood](https://expedia.ca/Greenwood-Vacation-Rentals.d110848.Travel-Guide-VacationRentals)[Greenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Greenwood.d110848.Car-Rental-Guide)[Greenwood Vacation Packages](https://expedia.ca/Greenwood.d110848.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Greenwood Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=110848&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=110848&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=110848&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=110848&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Greenwood Vacation Homes ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119760000/119752500/119752487/bd56d68f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119760000/119752500/119752487/a59a22ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119760000/119752500/119752487/36487deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119760000/119752500/119752487/4ffa7fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic home, great yard & Walk to Dogfish Head Brewery! Milton 10/10 Exceptional (3) "Enjoyed the house very clean liked the area. " CA $127 CA $266 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Milton-Hotels-Historic-4-BR-Walk-To-Dogfish-Head-Brewery.h119752487.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/cb8b4409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/60a789b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/146a30dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/5dbbfb34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poe Themed Home Close to Beaches and DE Turf Milford 10/10 Exceptional (4) "Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. " CA $227 CA $390 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Milford-Hotels-Poe-Themed-Home-Close-To-Beaches-And-DE-Turf.h112759073.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/95000000/94970000/94960400/94960322/1db12af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94970000/94960400/94960322/80bdc9cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94970000/94960400/94960322/eeb41ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94970000/94960400/94960322/9c2a972c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly! Milford 9.6/10 Exceptional (16) "An amazing beach area that shows the oceans natural beauty! Neighborhood is extremely quiet and welcoming. " CA $195 CA $517 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Milford-Hotels-Spacious-Home-Steps-Away-From-Quiet-Beach-Nature-And-Wildlife-Pet-Friendly.h94960322.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103800000/103798400/103798394/be30cd04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103800000/103798400/103798394/5132ef51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/104000000/103800000/103798400/103798394/5024835f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103800000/103798400/103798394/f4e9e6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower Milton 9.8/10 Exceptional (10) "Wonderful property! Through the dune and on the beach. The house was clean and comfortable. We had a wonderful family vacation at this restful location. If you enjoy a beach without large amounts of people this is for you!" CA $189 CA $464 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Milton-Hotels-Waterfront-Getaway-Amazing-Location-Large-Backyard.h103798394.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74040000/74034300/74034263/d0bc5c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74040000/74034300/74034263/086b8b14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/75000000/74040000/74034300/74034263/1e232bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74040000/74034300/74034263/5a7035da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coastal Cottage 15 Minutes to Lewes Beach + Bike Trail Access. Milton 10/10 Exceptional (29) "Enjoyed our stay at this property! It is comfortable, with room for many people, and a short drive to the beach." CA $226 CA $572 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Milton-Hotels-Coastal-Cottage-In-Milton-With-Bike-Trail-Access-To-Downtown-Lewes.h74034263.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118650000/118649100/118649066/13740f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118650000/118649100/118649066/b0bd07df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118650000/118649100/118649066/643b774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/119000000/118650000/118649100/118649066/0ba5233b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New 3‑BR Ranch by DE Turf & Beaches Lincoln 10/10 Exceptional (2) "Beautiful accommodations that are very comfortable. We would stay there again." CA $139 CA $336 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Lincoln-Hotels-New-3BR-Ranch-By-DE-Turf-Beaches.h118649066.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/35000000/34340000/34339600/34339534/c1583d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34340000/34339600/34339534/dfd85ce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34340000/34339600/34339534/1b38d205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34340000/34339600/34339534/89833bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delaware Beachfront Private Getaway on the Bay Milford 9.8/10 Exceptional (191) "Wonderful place for nature, peace, and quiet. Beautiful sunrises every morning. A great getaway." CA $337 CA $835 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Milford-Hotels-Delaware-Beachfront-Private-Getaway-On-The-Bay.h34339534.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w449h683x288y0-03622767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h675x0y4-d4e73536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h676x0y4-1256b46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h675x0y4-d63d4766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5 Bedroom w/Pool, Patio and Theater Magnolia 9.8/10 Exceptional (7) "Great house for a large family " CA $339 CA $926 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Magnolia-Hotels-Spacious-5-Bedroom-WPatio.h100285322.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/a1d87464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/1e473e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/7fda792d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/f9a95f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turnbridge Manor Denton 9.8/10 Exceptional (12) "We rented this wonderful home for Christmas and had the most relaxing time. The house is just as advertised and the owner a delight to work with. We especially loved the proximity to the square and how walkable it was to everything. I can’t wait to rent it again during warm weather to enjoy all the wonderful porches and the outdoor area." CA $504 CA $854 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115890000/115881100/115881100/20564de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115890000/115881100/115881100/2d80968d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/116000000/115890000/115881100/115881100/5eb63166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115890000/115881100/115881100/cdc215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Come Be Our Guest At A Place of Peace Harbeson CA $252 CA $402 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Milton-Hotels-Come-Be-Our-Guest-At-A-Place-Of-Peace.h115881100.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111350000/111344300/111344245/2b78cba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111350000/111344300/111344245/f748face.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, table tennis, books](https://images.trvl-media.com/lodging/112000000/111350000/111344300/111344245/5a405423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/112000000/111350000/111344300/111344245/a9e6c1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lewes beach relax hot-tub games Lewes 10/10 Exceptional (2) "Great location near the beach. Pleasant decor. Good supplies in kitchen. Enjoyed having beach supplies at our disposal. Hot tub and outside grill area was a plus." CA $797 CA $1,706 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Lewes-Hotels-Lewes-Beach-Relax-Hot-Tub-Games.h111344245.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103110000/103102300/103102238/6a971eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103110000/103102300/103102238/3401d004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103110000/103102300/103102238/3b5f8264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103110000/103102300/103102238/fbb1b937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH Lewes 8.8/10 Excellent (17) "This home is beautiful and clean and perfectly located for us to take advantage of the beaches as well as the baseball tournament that our grandson was in. The Host was very responsive and we thoroughly enjoyed our stay here." CA $641 CA $922 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Lewes-Hotels-Cozy-Four-Br-Home-W-Amazing-Sunsets-Only-Minutes-To-DEMD-Beaches-Come-Enjoy.h103102238.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29®ionId=110848&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FGreenwood-Private-Vacation-Homes.d110848-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FGreenwood-Private-Vacation-Homes.d110848-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Greenwood Hotel Reviews ![Hampton Inn Milford](//images.trvl-media.com/lodging/4000000/3650000/3645000/3644980/3ed7ec07_y.jpg) ### Hampton Inn Milford 10/10 Excellent "The staff was very kind, our stay was quiet and peaceful" [](https://expedia.ca/Dover-Hotels-Hampton-Inn-Milford.h3644980.Hotel-Information) ![Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches](//images.trvl-media.com/lodging/9000000/8750000/8740800/8740727/1c6278af_y.jpg) ### Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches 10/10 Excellent "This was a great hotel. We only stayed 1 night, but we didn't arrive until late. Someone was at the front desk when we arrived and check-in was easy. The room was clean and the property felt safe. Checked all of the boxes for me for a good night's sleep on a road trip." [](https://expedia.ca/Rehoboth-Beach-Hotels-Microtel-Inn-Suites-By-Wyndham-Georgetown-Delaware-Beaches.h8740727.Hotel-Information) ![Microtel Inn & Suites by Wyndham Dover](//images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg) ### Microtel Inn & Suites by Wyndham Dover 10/10 Excellent "Convenient and reasonable!!" [](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.Hotel-Information) ![Home2 Suites by Hilton Lewes Rehoboth Beach](//images.trvl-media.com/lodging/47000000/46230000/46227200/46227151/17672712_y.jpg) ### Home2 Suites by Hilton Lewes Rehoboth Beach 10/10 Excellent "Beauty rooms, lot of parking. Very friendly staff. Highly recommend this hotel" [](https://expedia.ca/Rehoboth-Beach-Hotels-Home2-Suites-By-Hilton-Lewes-Rehoboth-Beach.h46227151.Hotel-Information) ![Home2 Suites by Hilton Dover, DE](//images.trvl-media.com/lodging/1000000/30000/26700/26691/w3837h2558x3y3-b9ccd77d_y.jpg) ### Home2 Suites by Hilton Dover, DE 10/10 Excellent "Brandon was Great at check in!" [](https://expedia.ca/Dover-Hotels-Home2-Suites-By-Hilton-Dover.h26691.Hotel-Information) ![Best Western Plus Easton Inn & Suites](//images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b_y.jpg) ### Best Western Plus Easton Inn & Suites 10/10 Excellent "Excellent staff, very clean room, good hotel breakfast " [](https://expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Microtel Inn & Suites by Wyndham Milford](//images.trvl-media.com/lodging/65000000/64920000/64916800/64916777/3f703075_y.jpg) ### Microtel Inn & Suites by Wyndham Milford 10/10 Excellent "Lovely room, clean, very helpful and friendly staff and a great location with a lot of stores and dining options around at a great price. Enjoyed my stay! " [](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Milford.h64916777.Hotel-Information) ![Hyatt House Lewes/Rehoboth Beach](//images.trvl-media.com/lodging/67000000/66940000/66935600/66935541/de682f27_y.jpg) ### Hyatt House Lewes/Rehoboth Beach 10/10 Excellent "Staying here with a pet was made easy by the staff and areas to walk my dog. The staff was very friendly and helpful, from check in to check out. The only issue I had was that the refrigerator did not keep food cold or even cool. The staff offered to have someone look at it but i declined. My wife is funny about people in the room." [](https://expedia.ca/Rehoboth-Beach-Hotels-Hyatt-House-LewesRehoboth-Beach.h66935541.Hotel-Information) ![Tru by Hilton Georgetown](//images.trvl-media.com/lodging/37000000/36250000/36247600/36247517/43c13260_y.jpg) ### Tru by Hilton Georgetown 10/10 Excellent "Excellent everything. Breakfast was awesome. Never saw a pancake or yogurt makers like that. Nicely decorated. Clean." [](https://expedia.ca/Rehoboth-Beach-Hotels-Tru-By-Hilton-Georgetown.h36247517.Hotel-Information) ## Find out more about Greenwood ## Greenwood Vacation Homes information | Number of reviews | 248 | | --- | --- | | Accommodation | 356 Vacation Homes | | Lowest Price | CA $266 | | Highest Price | CA $1,706 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Blades Hotels](https://www.expedia.ca/Blades-Hotels.d553248634999426799.Travel-Guide-Hotels) - [Cheap Hotels in Bridgeville](https://www.expedia.ca/Bridgeville-Hotels-Cheap-Hotels.0-0-d82882-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Bridgeville](https://www.expedia.ca/Bridgeville-Hotels-Pet-Friendly-Hotel.0-0-d82882-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Bridgeville Hotels](https://www.expedia.ca/Bridgeville-Hotels.d82882.Travel-Guide-Hotels) - [Hotels near Delaware State Fairgrounds](https://www.expedia.ca/Delaware-State-Fairgrounds-Hotels.0-l6127268-0.Travel-Guide-Filter-Hotels) - 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