Fall & Winter Escapes in Southern Maine — Save 20% When You Book Direct 

Book Select Properties in October with code DIRECTOCT for stays October 31 – December 31, 2025 

Good to know: Our rates are already seasonally adjusted for fall & early winter seasons. The code takes an additional 20% off when you book on our website. 

Whether you’ve never stayed with us, you’re a past guest, or you already have an upcoming trip on the calendar, this is the perfect time to enjoy the quieter side of the coast—and lock in real savings by booking direct.

Why book direct now? 

Seasonal pricing + extra savings: rates already reflect the season; DIRECTOCT takes another 20% off at checkout for select homes 

Best rate is direct: the code works only on our site (not Airbnb/VRBO). 

Cozy shoulder season: brilliant foliage, holiday lights, fireplaces, and peaceful beaches with fewer crowds. 

How it works: Book on our website Oct 1 – 31, 2025 for stays Oct – Dec 2025. Enter DIRECTOCT at checkout. Offer valid on select properties.

Pick Your Vibe 

Ogunquit — Galleries, Coastal Path, Festive Weekends (5 Available Homes)

Perfect for couples, families, art lovers, and foodies. (Seasonal rates in effect; use DIRECTOCT for an extra 20% off on select homes.) 

433 Main Street — Sleeps 189BR • 10 BA (14 starting November) 

Book this home The Nathaniel Scott House with a Seasonal Carriage House Close to Downtown and Beaches 

60 River RoadThe ultimate romantic escape Sleeps 4 • 2 BR • 2.5 BA

181 Main Street — Sleeps 8 • 4 BR • 2BA  

Plus, more: 

View all Ogunquit homes Properties – Maine Street Property Management

Wells — Tidal Inlets & Easy Beach Walks (4 Available Homes) 

Perfect for families, birders, and long lowtide walks. (Seasonal rates in effect; use DIRECTOCT for an extra 20% off on select homes.) 

247 Ocean Avenue — Designer home, step onto beach. Sleeps 104BR • 4 BA 

518 Ocean Avenue — Immaculate, steps to the sand. Sleeps 105BR • 2 BA 

240 Island BeachDog-friendly, quiet beach. Sleeps 84BR • 2 BA 

Plus, more: 

View all Wells homes Properties – Maine Street Property Management

York Harbor — Classic Charm & Scenic Overlooks (3 Available Homes) 

Perfect for relaxation, slow mornings, scenic drives. (Seasonal rates in effect; use DIRECTOCT for an extra 20% off on select homes.) 

18 Lock Lane — Ocean views on rocky shores. Sleeps 12 • 5BR • 3BA  

402 York Street — Step back in time and gather. Sleeps 136BR • 4 BA 

12 Barrell Lane Extension — Charm + modern amenities. Sleeps 136BR • 4 BA  

Plus, more: 

View all York Harbor homes Properties – Maine Street Property Management

Fall & Holiday Events (Oct–Dec) 

Anchor a long weekend around local favorites: 

York Harvestfest October 18 (Short Sands, York Beach) 

Big artisan fair, live music, food, Kidsfest. Great fall, family-friendly day at Short Sands, York Beach. 

Leaf-peeping meets small-town festival. The whole village turns into a strollable fairground with artisan booths, a classic car show, kids’ activities, and cheeky happenings like the High Heel Dash. 

postcard coastal holiday—tree and bridge lightings, a cheerful parade, craft markets, and fireworks (weather permitting). Shops add seasonal windows; restaurants lean into cozy menus. 

A classic New England evening parade through York’s village with floats, music, and plenty of lights. Festive without being overwhelming. 

The most “small-town Maine” moment of the season—bands, floats, and local groups cruising down Route 1 with plenty of waves and candy canes. 

How to redeem your 20% off 

1) Choose any select property for dates Oct – Dec 2025. 

2) Book on our website (not on Airbnb/VRBO). 

3) At checkout, enter DIRECTOCT to apply 20% off. 

Book direct & save Maine Street Vacation Rentals

Prefer help choosing? Contact our team vacations@mainestreetpm.com  

Skye Ouellette

Owner / CEO

Skye is the CEO of Maine Street Property Management. She founded the company after leaving the corporate world, where she built a successful career as a consultant and project manager. Under her leadership, Maine Street has grown into a leading property management firm, known for its expertise and commitment to excellence.

Skye and her husband, Joe, are passionate about real estate, and experienced property investors, actively expanding their extensive portfolio of residential and commercial rental properties in the Wells area. From hands-on, sweat equity renovations in their investing early days to now having a full maintenance staff and overseeing multi-million dollar renovation projects, Skye and Joe have built a reputation as industry experts in real estate investment, property rehabilitation, and large-scale renovations. Skye has made it Maine Street’s mission to help real estate investors tap into this wealth of knowledge and continue building their portfolios with confidence.
 

As a licensed Real Estate Broker with Anne Erwin Sotheby’s International Realty in York, Skye is a real estate expert.  Her focus is 100% on running Maine Street, so she rarely is active in the sales world these days, however she strongly collaborates with her colleagues at Anne Erwin to provide comprehensive real estate services—from deal analysis and negotiation to purchase—seamlessly transitioning into full-service property management.

Outside of work, Skye enjoys spending time with her family and their dog, Charlie. She has a passion for flower gardening and loves taking in the beauty of Maine’s beaches.