Raymond Vacation Homes

A flowing river with large rocks, surrounded by trees and a snowy bank.

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Our top choices for Raymond holiday homes

A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

1. Cozy Family Home w/ Beach Access

Raymond

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

2. Cozy 2-bedroom house with shared beach access to Sebago Lake

Raymond

HK$2,190 total

includes taxes & fees

11 Oct - 12 Oct

A living room with a sofa, armchairs, a coffee table, and a patterned rug.

3. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

HK$4,004 total

includes taxes & fees

13 Oct - 14 Oct

A multi-story house with a dock and a children's play area.

4. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Casco

loie H.

HK$5,623 total

includes taxes & fees

14 Oct - 15 Oct

A wooden deck with a grill area, overlooking a lake with trees in the background.

5. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Casco

MaryAnn F.

HK$2,173 total

includes taxes & fees

12 Oct - 13 Oct

6. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Casco

Edward R.

HK$2,369 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

7. Fully Updated Lake View Home on Thomas Pond

Casco

HK$4,123 total

includes taxes & fees

12 Oct - 13 Oct

A cabin with a dock extending into a lake, surrounded by trees.

8. Long Lake 3BR: Beach Access + Dock

Naples

HK$4,209 total

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a bar area, wooden ceiling, and skylights.

9. The Barnhouse with hot tub

New Gloucester

Jen V.

HK$2,789 total

includes taxes & fees

13 Oct - 14 Oct

A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

10. Windham Lakefront: Fire Pit and Modern Comforts

Windham

Richard G.

HK$6,807 total

includes taxes & fees

28 Oct - 29 Oct

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Freeport

HK$2,955 total

includes taxes & fees

11 Oct - 12 Oct

A modern cabin with a large glass facade, a hot tub, and wooden steps leading to the entrance.

12. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

Gina P.

HK$7,245 total

includes taxes & fees

12 Oct - 13 Oct

A wooden cabin with a sloped roof, surrounded by snow-covered trees and a clear sky.

13. Manor Suite,cozy newly renovated,downtown & beach

Bridgton

Jennifer

HK$1,309 total

includes taxes & fees

28 Oct - 29 Oct

14. ANY BIG PARTY!!!!

Standish

Logan R.

HK$12,899 total

includes taxes & fees

15 Oct - 16 Oct

A beach with footprints, a person standing, and birds on the sand.

15. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Buxton

Annette

HK$2,677 total

includes taxes & fees

20 Oct - 21 Oct

A window with a view of a snowy landscape and bare trees.

16. Tranquility between the Lakes & Sea

Westbrook

HK$2,553 total

includes taxes & fees

14 Oct - 15 Oct

A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

17. Peaceful Barn Loft near Sebago Lake and Conway, NH

Hiram

HK$1,582 total

includes taxes & fees

13 Oct - 14 Oct

A dirt path in a park with autumn foliage.

18. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

Westbrook

Genevieve W.

HK$4,936 total

includes taxes & fees

12 Oct - 13 Oct

A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

19. The Outlet Studio, Rustic Comfort w Fireplace

Freeport

Joanne H.

HK$2,138 total

includes taxes & fees

11 Oct - 12 Oct

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

20. Luxe 5 Bed/ 3 Bath with Game Room & AC

Yarmouth

Michelle T.

HK$8,346 total

includes taxes & fees

13 Oct - 14 Oct

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Top Raymond Hotel Reviews

Portland Harbor Hotel

10/10 Excellent

"We liked the “pantry” on each floor. Coffee and snacks were perfect!"

Spark by Hilton Portland Airport Maine Mall

8/10 Good

"It was mostly good. Still carrying the Hilton name, I expected it to be nicer. But, on the other hand, I understand that they're taking an old hotel and giving it the Spark refresh. Airport shuttle was nice to have, though no grab-and-go breakfast options were available, despite the breakfast being grab-n-go in the first place. Nice people."

DoubleTree by Hilton Hotel Portland

10/10 Excellent

"I’m very happy with this hotel. The airport shuttle works perfectly. The front staff was very good. I can’t say enough nice things about the bar/breakfast employees, some of the nicest people I’ve ever met. The room was clean and spacious, the mattress and bedding were very good. Thank you Doubletree!"

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